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Anti-inflammatory analgesic drugs Indometacin CAS:53-86-1
Cas No: 53-86-1
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53-86-1 Usage

Clinical Use

Indomethacin is available for the short-term treatment of acute gouty arthritis, acute pain of ankylosing spondylitis, and osteoarthritis. An injectable form to be reconstituted also is available as the sodium trihydrate salt for IV use in premature infants with patent ductus arteriosus. Because of its ability to suppress uterine activity by inhibiting prostaglandin biosynthesis, indomethacin also has an unlabeled use to prevent premature labor.

Chemical Synthesis

Indomethacin, 1-(n-chlorobenzoyl)-5-methoxy-2-methylindol-3-acetic acid (3.2.51), has been synthesized by various methods. All of the proposed methods of synthesis start with 4-methoxyphenylhydrazine. According to the first method, a reaction is done to make indole from phenylhydrazone (3.2.46) by Fischer’s method, using levulinic acid methyl ester as a carbonyl component, hydrogen chloride as a catalyst, and ethanol as a solvent, to give the methyl ester of 5-methoxy-2-methyl-3-indolylacetic acid (3.2.47). This product is hydrolyzed by an alkali into 5-methoxy-2-methyl-3-indolylacetic acid (3.2.48), from which tert-butyl ester of 5-methoxy-2-methyl-3-indolylacetic acid (3.2.49) is formed by using tert-butyl alcohol and zinc chloride in the presence of dicyclohexylcarbodiimide. The resulting product undergoes acylation at the indole nitrogen atom by p-chorobenzoyl chloride in dimethylformamide, using sodium hydride as a base. The resulting tert-butyl ester of 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indolylacetic acid (3.2.50), further undergoes thermal decomposition to the desired acid, indomethacin (3.2.51) [111,112].

acute toxicity

Oral administration: LD50 2.42 mg/kg in rats; oral administration of 11.84 mg/kg of LD50: in mice.

Manufacturing Process

(A) 2-Methyl-5-Merhoxy-3-Indolylacetic Anhydride: Dicyclohexylcarbodiimide (10 g, 0.049 mol) is dissolved in a solution of 2-methyl-5-methoxy-3-indolylacetic acid (22 g, 0.10 mol) in 200 ml of THF, and the solution is allowed to stand at room temperature for 2 hours. The precipitated urea is removed by filtration, and the filtrate is evaporated in vacuo to a residue and flushed with Skellysolve 6. The residual oily anhydride is used without purification in the next step.(B) t-Butyl 2-Methyl-5-Merhoxy-3-Indolylacetate: t-Butyl alcohol (25 ml) and fused zinc chloride (0.3 g) are added to the anhydride from Part A. The solution is refluxed for 16 hours and excess alcohol is removed in vacuo. The residue is dissolved in ether, washed several times with saturated bicarbonate, water, and saturated salt solution. After drying over magnesium sulfate, the solution is treated with charcoal, evaporated, and flushed several times with Skellysolve B for complete removal of alcohol. The residual oily ester (18 g, 93%) is used without purification.(C) t-Buryl 1-p-Chlorobenzoyl-2-Methyl-5-Mefhoxy-3-Indolylacetate: A stirred solution of ester (18 g, 0.065 mol) in dry DMF (450 ml) is cooled to 4°C in an ice bath, and sodium hydride (4.9 g, 0.098 mol, 50% susp.) is added in portions. After 15 minutes, p-chlorobenzoyl chloride (15 g, 0.085 mol) is added dropwise during 10 minutes, and the mixture is stirred for 9 hours without replenishing the ice bath. The mixture is then poured into one liter of 5% acetic acid, extracted with a mixture of ether and benzene, washed thoroughly with water, bicarbonate, saturated salt, dried over magnesium sulfate, treated with charcoal, and evaporated to a residue which partly crystallizes. This is shaken with ether, filtered and the filtrate is evaporated to a residue (17 g) which solidifies after being refrigerated overnight.The crude product is boiled with 300 ml of Skellysolve 6, cooled to room temperature, decanted from some gummy material, treated with charcoal, concentrated to 100 ml, and allowed to crystallize. The product thus obtained (10 g) is recrystallized from 50 ml of methanol and gives 4.5 g of analytically pure material, MP 103° to 104°C.(D) 1 -p-Chlorobenzoyl-2-Methyl-5-Methoxy-3-Indolylacetic Acid: A mixture of 1 g ester and 0.1 g powdered porous plate is heated in an oil bath at 210°C with magnetic stirring under a blanket of nitrogen for about 2 hours. No intensification of color (pale yellow) occurs during this period. After cooling under nitrogen, the product is dissolved in benzene and ether, filtered, and extracted with bicarbonate. The aqueous solution is filtered with suction to remove ether, neutralized with acetic acid, and then acidified weakly with dilute hydrochloric acid. The crude product (0.4 g, 47%) is recrystallized from aqueous ethanol and dried in vacuo at 65°C: MP 151°C.

Uses

antiinflammatory, antipyretic, analgesic

Biological Functions

Indomethacin (Indocin) is an acetic acid derivative related functionally to sulindac (Clinoril), a prodrug with a long half-life, and etodolac (Lodine).They are metabolized in the liver and excreted as metabolites in the bile and via the kidney. They are potent inhibitors of COX and thus extremely effective antiinflammatory agents.

methods of production

Para aminophenylmethylether is through diazotization, reduction, cyclization, hydrolysis, acidification to get indomethacin.

anti-inflammatory analgesic

Indomethacin is a kind of stronger corticoid anti-inflammatory and antipyretic and analgesic, by inhibiting cyclooxygenase reducing the synthesis of prostaglandin (PG), to prevent the formation of the nere impulses, inflammation tissue inhibiting inflammatory reaction, including inhibition of leukocyte chemotaxis and lysosomal enzyme release, etc., and produce antipyretic, analgesic and anti-inflammatory effects. Indomethacin anti-inflammatory, antipyretic effect is very strong, its anti-inflammatory effect is better than bute, 84 times better than hydrocortisone, and sugar cortical hormone, used in combination with aspirin, bute, can reduce their dosage, toxic and side effects, improve curative effect; Second is antipyretic effect, 10 times than amidopyrine ;its analgesic action is weak , only to the inflammatory pain has obvious analgesic effect, but the effect is good for inflammatory pain than Baotai loose, analgin and salicylic acid. Clinical is mainly used for the salicylic acid, drugs are less tolerance or curative effect is not obvious in the acute and chronic rheumatic or rheumatoid arthritis, ankylosing spondylitis, slippery bursa phlogistic, tenosynovitis, articular capsulitis, osteoarthritis and acute gout and cancerous pain, etc.In recent years, the researchers try to use indomethacin biliary colic, dysmenorrhea, migraine, glomerulonephritis, polyuria, salmonella gastroenteritis, orthostatic hypotension, bart syndrome and so on, all have good curative effect.It can also be used to treat eye pigment meningitis, keratitis, scleritis, glaucoma and fever caused by cancer or other difficult to control the fever. Dermatologist for lupus erythematosus (sle), white plug syndrome, scleroderma, nodular erythema, herpes zoster, joint type of psoriasis, etc. photosensitive dermatitis induced by topical treatment of eczema, allergic dermatitis, and local pain.

General Description

Crystals.

Uses

1.The product is anti-inflammatory, and antipyretic effect is obvious, mainly is used for salicylates to tolerance or the effect is not significant rheumatism and arthritis, ankylosing light spondylitis, osteoarthritis. 2.Non steroid anti-inflammatory analgesic

usage and dosage

1.Anti-rheumatism: adult dosage: oral: early quantity from 25 to 50 mg each time, 2~4 times a day, immediately take at food service or after a meal. Such as good tolerance, the daily dosage can be increased from 25 to 50 mg per week, the most mount should not be more than 200 mg a day. Arthritis patients such as persistent pain at night or morning stiffness, can give quantity of 100 mg in bed all day. 2. Resistance to gout: oral: At the beginning quantity is 100 mg once, then 50 mg, three times a day, until the pain relief, and then gradually reduced as soon as possible, until the drug withdrawal. 3. Antifebrile: adult dosage: oral: 25~50 mg each time, 3~4 times daily.Rectal drug delivery: every time 50 mg, 50 to 100 mg per day. Pediatric dosage: oral: 0.5~1 mg/kg each time, 3 times a day. The above information is Chemicalbook Hanya edited.

Air & Water Reactions

Practically insoluble in water. Decomposes in alkali.

Chemical Properties

Crystalline Solid

matters need attention

1.indomethacin and aspirin have cross allergic. Caused by aspirin allergic asthmatic patients, the application of this product can be induced bronchospasm. Other non steroidal anti-inflammatory drugs to which are allergic may also be allergic to this product. 2.This product is contraindicated with active ulcer disease, ulcerative colitis and history, epilepsy, Parkinson's disease, mental disease, liver and kidney function, the goods or aspirin or other nonsteroidal anti-inflammatory drug allergic person, angioedema or bronchial asthma. This product for the last 3 months of pregnancy can make fetal ductus arteriosus closure and result in persistent pulmonary hypertension, so pregnant women, disabled. This product can be discharged from the milk, breast-feeding women also disable. 3.This product is used for patients with cardiac insufficiency, and hypertension (because this product sodium can lead to water retention, hemophilia and other patients with hemorrhagic disease (because this product can make the bleeding time prolonged, aggravate bleeding tendency), aplastic anemia, granulocytopenia disease patients (this product is inhibition of hematopoietic system).Age < 14 years old children should not be commonly used drug, When it is applied,it should be closely observed.Easily occur in elderly patients with renal toxicity, which should also be careful. 4.Because indomethacin has inhibition to the platelet aggregation, which can make the bleeding time prolonged, the role after the drug was stopped sustainable. During the blood urea nitrogen and serum creatinine,levels are also often higher. During the medication,it should be regularly check routine blood and liver and kidney function. Case reports referred to in this article that the product can lead to corneal composure and retinal change (including macular degeneration), if it comes to the blurred vision eye exams should be done immediately. 5.Drug overdose (especially when dose > 150 mg a day) is easy to cause toxic reactions such as nausea, vomiting, tension headaches, sleepiness, spirit, behavior disorders, etc., with vomiting or gastric lavage, symptomatic and supportive treatment.

Definition

The antiinflammatory drug indomethacin.

World Health Organization (WHO)

Indometacin was introduced in 1963 and it is one of the first NSAIDs. Convulsions are rarely reported in relation with the use of this group of agents. Indometacin farnesil is a pro-drug of indometacin, and the occurrence of gastro-intestinal adverse effects could be expected. See also under nonsteroidal antiinflammatory agents.

Fire Hazard

Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.

Category

Poisonous

Pharmaceutical Applications

Indomethacinis a nonsteroidal anti-inflammatory agent used in pain and moderate to severe inflammation in rheumatic diseases and other musculoskeletal disorders. It is a COX (cyclooxygenase) inhibitor and therefore interrupts the production of prostaglandins.

Extinguisher

Foam, fog water, sand, carbon dioxide.

Side effects

Adverse reactions of Indomethacin are high incidence , common adverse reactions are as follows: 1. nausea, vomiting, abdominal pain, diarrhea, anorexia, serious ulcers can occur and cause bleeding and perforation. After dinner, that can reduce the incidence. 2. common headache, dizziness, fatigue, occasional seizures, mental derangement, syncope, etc. Should be paid attention to in due course. 3.the skin pruritus, erythema, urticaria, and one of the few of asthma, breathing problems and even breathing, circulation inhibition. 4.Inhibition of hematopoietic system such as granulocytopenia, aplastic anemia, thrombocytopenia, and so on. Although rare, but more severe consequences.There are also some other similar to aspirin reaction, notes are also the same.

Therapeutic Function

Antiinflammatory

Side effects

All of these drugs produce analgesic effects, antipyresis, and antiinflammatory effects.Due to the high incidence of gastric irritation, headache, nausea, and other side effects, including hematological effects and coronary vasoconstriction, they are not useful as an initial treatment for pain. GI irritation and ulceration occur to a lesser extent with etodolac. Indomethacin is useful in the treatment of acute gout, osteoarthritis, ankylosing spondylitis, and acceleration of the closure of the ductus arteriosus in premature infants. The tocolytic effects of indomethacin to prevent preterm labor are the result of its effects on prostaglandin synthesis. However, the toxicity of the drug limits such application, since it increases fetal morbidity. Indomethacin is contraindicated in pregnancy, in asthmatics, and in those with gastric ulcers or other ulceration of the GI tract. Indomethacin may increase the symptoms associated with depression or other psychiatric disturbances and those associated with epilepsy and Parkinson’s disease. The drug should be used with caution in such patients.

Originator

Indocin,MSD,US,1965

Brand name

Indocin (Merck);Argan.

Pharmaceutical Applications

Indomethacin is a nonsteroidal anti-inflammatory agent used in pain and moderate to severe inflammation in rheumatic diseases and other musculoskeletal disorders. It is a COX (cyclooxygenase) inhibitor and therefore interrupts the production of prostaglandins. A series of new silicon compounds, based on the structure of indomethacin, have been synthesised and are under investigation as novel anticancer agents. The carboxyl group of indomethacin was reacted with a series of amino-functionalised silanes. The resulting products have been shown to be significantly more lipophilic and more selective to COX-2. Furthermore, in vitro testing has shown an increased uptake of the new compounds at the tumour site. The silane-functionalised indomethacin derivatives exhibited a 15-fold increased antiproliferative effect when tested against pancreatic cancer .

Reactivity Profile

A weak organic acid.

classification of toxicity

Highly toxic.

Uses

Inhibits cyclooxygenase (IC50=0.1uM) selectively over liposygenases (IC50=100uM for 5-,12- and 15-LO). A clinically useful NAISD

Indications

Indomethacin (Indocin) is used in the treatment of acute gouty arthritis, rheumatoid arthritis, ankylosing spondylitis, and osteoarthritis. It is not recommended for use as a simple analgesic or antipyretic because of its potential for toxicity.While indomethacin inhibits both COX-1 and COX-2, it is moderately selective for COX- 1. It produces more CNS side effects than most of the other NSAIDs. Severe headache occurs in 25 to 50% of patients; vertigo, confusion, and psychological disturbances occur with some regularity. GI symptoms also are more frequent and severe than with most other NSAIDs. Hematopoietic side effects (e.g., leukopenia, hemolytic anemia, aplastic anemia, purpura, thrombocytopenia, and agranulocytosis) also may occur. Ocular effects (blurred vision, corneal deposits) have been observed in patients receiving indomethacin, and regular ophthalmological examinations are necessary when the drug is used for long periods. Hepatitis, jaundice, pancreatitis, and hypersensitivity reactions also have been noted.

Biological Activity

Cyclooxgenase (COX) inhibitor; displays selectivity for COX-1 (IC 50 values are 230 and 630 nM for human COX-1 and COX-2 respectively). Widely used anti-inflammatory agent.

General Description

From the time of its introduction in 1965, indomethacin(Indocin) has been widely used as an analgesic to relieve inflammatorypain associated with RA, OA and ankylosingspondylitis, and, to a lesser extent, in gout. Although both itsanalgesic and anti-inflammatory activities are well established,its use is often limited because of frequent GI distressand potential drug interactions, especially with warfarinfurosemide, and lithium (i.e., it elevates blood levels oflithium as a result of reducing renal blood flow and thereforeincreases lithium toxicities).Following oral administration, indomethacin is rapidlyabsorbed and is 90% protein bound at therapeutic plasmaconcentrations. The drug has a biological half-life ofabout 5 to 10 hours and a plasma clearance of 1 to 2.5 ml/kgper minute. It is metabolized to its inactive, O-desmethyl,N-deschlorobenzoyl-, and O-desmethyl, N-deschlorobenzoylindomethacinmetabolites.

Used in Particular Diseases

Acute Gouty Arthritis: Dosage and Frequency:?25–50 mg four times a day for 3 days, then taper to twice daily for 4–7 days

Pharmacokinetics

Oral medicine absorbed quickly and completely, can absorb more than 90% of the dosage of food with in 4 h, take medicine of acid containing aluminum and magnesium can be slightly slowed absorption, plasma protein conjugation rate is about 99%. After oral 25 mg, tmax is 1~4 h, the blood medicine peak concentration (Cmax) is 1.4 mu g/ml, when 50 mg, Cmax is 2.8 mu g/ml; Half-life (t1/2) of an average is 4.5 h, premature extended obviously. A small amount of indomethacin can through the blood-brain barrier. And through the placenta.This article in the liver metabolism go methyl chloride and chlorobenzene formyl chloride, and can be hydrolyzed into recycle indomethacin to absorb. Renal excretion from 60%, 10%~20% in prototype discharge; Part with droppings.33% from the bile excretion, 1.5% were prototype;In the breast milk also has a discharge (up to 0.5~2.0 mg daily).This product can not be dialysis to remove.

Combustible hazard characteristics

Open flame fuel; high heat decomposition of toxic chloride and nitrogen oxide gas.

Uses

Indomethacin is used in rheumatoid arthritis, nonspecific infectious polyarthritis, gouty arthritis, osteoarthritis, ankylosing spondylitis, arthrosis, back pain, neuralgia, myalgia, and other diseases accompanied by inflammation.

Storage and transportation characteristics

Low temperature and dry air ventilation; and oxidant, food additives separately.

Description

Aqueous solutions of indomethacin are not stable because of the ease of hydrolysis of the p-chlorobenzoyl group. The original synthesis of indomethacin by Shen et al. involved the formation of 2-methyl-5-methoxyindole acetic acid and subsequent acylation after protection of the carboxyl group as the t-butyl ester. It was introduced in the United States in 1965. It is still one of the most potent NSAIDs in use. It also is a more potent antipyretic than either aspirin or acetaminophen, and it possesses approximately 10 times the analgetic potency of aspirin.

chemical property

White or slightly yellow crystalline powder. Melting point is 158-162℃, soluble in acetone, slightly soluble in ethanol, chloroform, ether, almost insoluble in water.
InChI:InChI=1/C19H16ClNO4/c1-11-15(10-18(22)23)16-9-14(25-2)7-8-17(16)21(11)19(24)12-3-5-13(20)6-4-12/h3-9H,10H2,1-2H3,(H,22,23)/p-1

53-86-1 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (I0655)  Indomethacin  >98.0%(HPLC)(T) 53-86-1 25g 470.00CNY Detail
TCI America (I0655)  Indomethacin  >98.0%(HPLC)(T) 53-86-1 100g 990.00CNY Detail
TCI America (I0655)  Indomethacin  >98.0%(HPLC)(T) 53-86-1 500g 2,890.00CNY Detail
Alfa Aesar (A19910)  Indomethacin, 98%    53-86-1 5g 246.0CNY Detail
Alfa Aesar (A19910)  Indomethacin, 98%    53-86-1 25g 981.0CNY Detail
Alfa Aesar (A19910)  Indomethacin, 98%    53-86-1 100g 1953.0CNY Detail
Sigma-Aldrich (PHR1247)  Indomethacin  pharmaceutical secondary standard; traceable to USP and PhEur 53-86-1 PHR1247-500MG 878.44CNY Detail
Sigma-Aldrich (I0200000)  Indomethacin  European Pharmacopoeia (EP) Reference Standard 53-86-1 I0200000 1,880.19CNY Detail
USP (1341001)  Indomethacin  United States Pharmacopeia (USP) Reference Standard 53-86-1 1341001-200MG 4,662.45CNY Detail
Sigma (I7378)  Indomethacin  ≥99% (TLC) 53-86-1 I7378-5G 533.52CNY Detail
Sigma (I7378)  Indomethacin  ≥99% (TLC) 53-86-1 I7378-10G 1,168.83CNY Detail
Sigma (I7378)  Indomethacin  ≥99% (TLC) 53-86-1 I7378-25G 2,390.31CNY Detail

53-86-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name indometacin

1.2 Other means of identification

Product number -
Other names Lausit

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:53-86-1 SDS

53-86-1Synthetic route

indomethacin ethyl ester
16401-99-3

indomethacin ethyl ester

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol; water for 1h; Reflux;99%
With lithium hydroxide monohydrate In water at 25℃; for 6h;657 mg
5-Methoxy-2-methylindole-3-acetic acid
2882-15-7

5-Methoxy-2-methylindole-3-acetic acid

4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
Stage #1: 5-Methoxy-2-methylindole-3-acetic acid With potassium tert-butylate In tetrahydrofuran at -78℃; for 1h; Large scale;
Stage #2: 4-chloro-benzoyl chloride In tetrahydrofuran at 20℃; for 16h; Large scale;
97%
Stage #1: 5-Methoxy-2-methylindole-3-acetic acid With potassium tert-butylate In tetrahydrofuran at -78℃; for 1h;
Stage #2: 4-chloro-benzoyl chloride In tetrahydrofuran at 20℃; for 16h;
95%
With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hexamethylsilazane 1.) THF; Multistep reaction;
4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

ethyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate
17536-38-8

ethyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
Stage #1: ethyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.333333h; Inert atmosphere;
Stage #2: 4-chloro-benzoyl chloride In tetrahydrofuran at 25℃; for 10h; Inert atmosphere;
Stage #3: With lithium hydroxide monohydrate; water In tetrahydrofuran at 25℃; for 6h; Inert atmosphere;
92%
<1-(4-chlorobenzoyl)-2-methyl-5-methoxyindol-3-yl>acetaldehyde
24438-49-1

<1-(4-chlorobenzoyl)-2-methyl-5-methoxyindol-3-yl>acetaldehyde

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With N-hydroxyphthalimide; oxygen In acetonitrile at 80℃; for 30h; Schlenk technique;91%
With N-hydroxyphthalimide; oxygen In acetonitrile at 30℃; under 760.051 Torr; for 3h; Schlenk technique;91%
With sodium chlorite; sodium dihydrogenphosphate In tetrahydrofuran; water; tert-butyl alcohol at 20℃; for 0.5h; Schlenk technique;78%
With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene In tetrahydrofuran; water; tert-butyl alcohol at 20℃; for 0.5h;28.4 mg
2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid benzyl ester
26001-79-6

2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid benzyl ester

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 0.666667h;84%
With palladium 10% on activated carbon; hydrogen In ethyl acetate
With 10% Pd/C; hydrogen In ethyl acetate
indomethacin methyl ester
1601-18-9

indomethacin methyl ester

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With pyridine; lithium iodide for 20h; Reflux;84%
Stage #1: indomethacin methyl ester With pyridine; lithium iodide for 20h; Reflux;
Stage #2: With hydrogenchloride; water at 0℃;
83%
With pyridine; lithium iodide for 20h; Reflux;83%
acemetacin tert-butyl ester
75302-98-6

acemetacin tert-butyl ester

A

C20H18ClNO3

C20H18ClNO3

B

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With pyridine; iodine; aluminium In acetonitrile at 80℃; for 18h; chemoselective reaction;A 20%
B 70%
sodium 2-(4-chlorobenzoyl)-2-(4-methoxyphenyl)-1-hydrazosulfonate

sodium 2-(4-chlorobenzoyl)-2-(4-methoxyphenyl)-1-hydrazosulfonate

levulinic acid
123-76-2

levulinic acid

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With formic acid In acetic acid for 6h; Heating;66%
acemetacin tert-butyl ester
75302-98-6

acemetacin tert-butyl ester

A

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

B

acemetacin
53164-05-9

acemetacin

Conditions
ConditionsYield
With iodine; aluminium In acetonitrile at 20℃; for 6h; chemoselective reaction;A 30%
B 66%
5-methyl-2-furanone
591-12-8

5-methyl-2-furanone

N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine
16390-07-1

N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine

A

5-Methoxy-2-methylindole-3-acetic acid
2882-15-7

5-Methoxy-2-methylindole-3-acetic acid

B

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With sulfuric acid In acetonitrile for 24h; Fischer indole reaction; Heating;A n/a
B 65%
4-methoxyphenylhydrazine hydrochloride
19501-58-7

4-methoxyphenylhydrazine hydrochloride

4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

levulinic acid
123-76-2

levulinic acid

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
Stage #1: 4-methoxyphenylhydrazine hydrochloride With aldehyde resin; triethylamine In dichloromethane at 45℃;
Stage #2: 4-chloro-benzoyl chloride With pyridine at 80℃;
Stage #3: levulinic acid With trifluoroacetic acid In 1,2-dichloro-ethane at 70℃;
63%
Stage #1: 4-methoxyphenylhydrazine hydrochloride With polystyrene aldehyde resin; triethylamine In 1,2-dichloro-ethane at 45℃;
Stage #2: 4-chloro-benzoyl chloride With pyridine at 80℃;
Stage #3: levulinic acid With trifluoroacetic acid In 1,2-dichloro-ethane at 70℃;
1-(4-Chlorbenzoyl)-5-methoxy-2-methyl-1H-indolyl-3-essigsaeure-2-oxo-propylester
137138-23-9

1-(4-Chlorbenzoyl)-5-methoxy-2-methyl-1H-indolyl-3-essigsaeure-2-oxo-propylester

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With buffer pH 8.0 In 1,4-dioxane; acetonitrile at 57℃; half-life time of hydrolysis at different pH;
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetoxy]-2'-hydroxy-diethyloxide
78458-11-4

2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetoxy]-2'-hydroxy-diethyloxide

A

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

B

diethylene glycol
111-46-6

diethylene glycol

Conditions
ConditionsYield
With isotonic phosphate buffer at 32℃; chemical and enzymatic stability; other temperature and reagents, other pH; other olygoethylene derivatives as substrates;
(1,3-dioxo-2,3-dihydro-1H-2-isoindolyl)methyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-3-indolyl]acetate

(1,3-dioxo-2,3-dihydro-1H-2-isoindolyl)methyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-3-indolyl]acetate

A

phthalimide
136918-14-4

phthalimide

B

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With phosphate buffer pH 7.4 In 1,4-dioxane; water at 37℃; for 6h; Rate constant; var. of pH, also in rabbit plasma;
4‐formylphenyl 2‐(1‐(4‐chlorobenzoyl)‐5‐methoxy‐2‐methyl‐1H‐indol‐3‐yl)acetate

4‐formylphenyl 2‐(1‐(4‐chlorobenzoyl)‐5‐methoxy‐2‐methyl‐1H‐indol‐3‐yl)acetate

A

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

B

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With water In 1,4-dioxane at 37℃; Rate constant; t1/2; also without alkali;
[1-(4-Chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 2-formyl-phenyl ester

[1-(4-Chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 2-formyl-phenyl ester

A

salicylaldehyde
90-02-8

salicylaldehyde

B

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With water In 1,4-dioxane at 27℃; Kinetics; Thermodynamic data; other temp.; ΔH (excit.), ΔS (excit.); t1/2; also without alkali;
[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 2,5-dioxo-pyrrolidin-1-ylmethyl ester
1026091-18-8

[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 2,5-dioxo-pyrrolidin-1-ylmethyl ester

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With Tween 80; potassium chloride In phosphate buffer at 37℃; pH=7.4; Kinetics; Further Variations:; pH-values; also in 80 percent human plasma or 10 percent rat liver homogenate; Hydrolysis;
[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 2,3-dioxo-2,3-dihydro-indol-1-ylmethyl ester
1026676-65-2

[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 2,3-dioxo-2,3-dihydro-indol-1-ylmethyl ester

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With Tween 80; potassium chloride In phosphate buffer at 37℃; pH=7.4; Kinetics; Further Variations:; pH-values; also in 80 percent human plasma or 10 percent rat liver homogenate; Hydrolysis;
acemetacin
53164-05-9

acemetacin

A

5-Methoxy-2-methylindole-3-acetic acid
2882-15-7

5-Methoxy-2-methylindole-3-acetic acid

B

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

C

5-methoxy-2-methylindol-3-yl acetic acid carboxymethyl ester

5-methoxy-2-methylindol-3-yl acetic acid carboxymethyl ester

D

para-chlorobenzoic acid
74-11-3

para-chlorobenzoic acid

Conditions
ConditionsYield
In water at 30℃; Kinetics; Further Variations:; pH-values; Temperatures;
C23H20ClN3O4

C23H20ClN3O4

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With water In acetonitrile at 39℃; pH=7.1; Kinetics;
1-(4-Chlorbenzoyl)-5-methoxy-2-methyl-3-indolylessigsaeure-(2-diethylamino)ethylester
78667-03-5

1-(4-Chlorbenzoyl)-5-methoxy-2-methyl-3-indolylessigsaeure-(2-diethylamino)ethylester

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With pooled human serum at 37℃; Kinetics;
[2-(1-pyrrolidino)]ethyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetate

[2-(1-pyrrolidino)]ethyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetate

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With pooled human serum at 37℃; Kinetics;
[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid 2-piperidin-1-yl-ethyl ester

[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid 2-piperidin-1-yl-ethyl ester

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With pooled human serum at 37℃; Kinetics;
[2-(4-morpholino)]ethyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetate

[2-(4-morpholino)]ethyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetate

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With pooled human serum at 37℃; Kinetics;
1-(4-Chlorbenzoyl)-5-methoxy-2-methyl-3-indolylessigsaeure-(2-dimethylamino)ethylester
76812-37-8

1-(4-Chlorbenzoyl)-5-methoxy-2-methyl-3-indolylessigsaeure-(2-dimethylamino)ethylester

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
With pooled human serum at 37℃; Kinetics;
sodium 2-(4-methoxyphenyl)diazene-1-sulfonate
5354-81-4

sodium 2-(4-methoxyphenyl)diazene-1-sulfonate

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 75 percent / Zn; aq. AcOH / 4 h / 20 °C
2: 88 percent / AcONa / acetic acid / 6 h
3: 66 percent / HCOOH / acetic acid / 6 h / Heating
View Scheme
4-methoxy-aniline
104-94-9

4-methoxy-aniline

4-[Ph2(AcO)2Bi]-C6H4-OCH2-polystyrene cross-linked with divinylbenzene

4-[Ph2(AcO)2Bi]-C6H4-OCH2-polystyrene cross-linked with divinylbenzene

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: aq. HCl; NaNO2 / 0.5 h / -5 - 0 °C
1.2: 38 g / aq. Na2SO3; NaOH / 0.5 h / 5 °C
2.1: 75 percent / Zn; aq. AcOH / 4 h / 20 °C
3.1: 88 percent / AcONa / acetic acid / 6 h
4.1: 66 percent / HCOOH / acetic acid / 6 h / Heating
View Scheme
4-Methoxyphenylhydrazin-β-sulfonsaeure Natriumsalz

4-Methoxyphenylhydrazin-β-sulfonsaeure Natriumsalz

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 88 percent / AcONa / acetic acid / 6 h
2: 66 percent / HCOOH / acetic acid / 6 h / Heating
View Scheme
N-(4-chlorobenzoyl)-2-iodo-4-methoxyaniline
873657-14-8

N-(4-chlorobenzoyl)-2-iodo-4-methoxyaniline

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 54 percent / tri-2-furylphosphine; CuI; Pd2(dba)3 / Bu4NCl / dimethylformamide / 2 h / 20 °C
2: TBAF; AcOH / tetrahydrofuran / 5 h / 20 °C
3: IBX / ethyl acetate / 2 h / 80 °C
4: 28.4 mg / 2-methyl-2-butene; NaH2PO4*H2O; NaClO2 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 0.5 h / 20 °C
View Scheme
1-Adamantanamine
768-94-5

1-Adamantanamine

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

C19H16ClNO4*C10H17N

C19H16ClNO4*C10H17N

Conditions
ConditionsYield
In methanol at 20℃;100%
tert-butyl (2,2-difluoro-3-hydroxypropyl)carbamate

tert-butyl (2,2-difluoro-3-hydroxypropyl)carbamate

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

C27H29ClF2N2O6

C27H29ClF2N2O6

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃;100%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid 2,5-dioxopyrrolidin-1-yl ester
104425-42-5

[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid 2,5-dioxopyrrolidin-1-yl ester

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 3h;99%
With dicyclohexyl-carbodiimide In DMF (N,N-dimethyl-formamide); dichloromethane at 0 - 20℃;92%
With dicyclohexyl-carbodiimide In 1,4-dioxane for 8h; Ambient temperature;91%
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

4‐formylphenyl 2‐(1‐(4‐chlorobenzoyl)‐5‐methoxy‐2‐methyl‐1H‐indol‐3‐yl)acetate

4‐formylphenyl 2‐(1‐(4‐chlorobenzoyl)‐5‐methoxy‐2‐methyl‐1H‐indol‐3‐yl)acetate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h;99%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;28%
With pyridine; toluene-4-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide 1.) r.t., 24 h, 2.) 4 deg C, 24 h; Yield given. Multistep reaction;
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Indomethacin amide
6264-33-1

Indomethacin amide

Conditions
ConditionsYield
Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With oxalyl dichloride In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;
Stage #2: With ammonium hydroxide In tetrahydrofuran at 0℃; for 1h;
99%
With N-cyclohexyl-N'-(2-morpholinoethyl)carbodiimide para-toluenesulfonate; ammonia; benzotriazol-1-ol In 1,4-dioxane; DMF (N,N-dimethyl-formamide); ethyl acetate at 0 - 20℃;95%
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; ammonium chloride; benzotriazol-1-ol In N,N-dimethyl-formamide at 20℃; Substitution;84%
n-Pent-4-enyl alcohol
821-09-0

n-Pent-4-enyl alcohol

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

pent-4-en-1-yl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate
1019777-27-5

pent-4-en-1-yl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere;99%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 40h; Inert atmosphere;87%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 48h; Inert atmosphere;84%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h; Schlenk technique; Inert atmosphere;30%
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

(4-chlorophenyl)(3-(2-hydroxyethyl)-5-methoxy-2-methyl-1H-indol-1-yl)methanone
16130-32-8

(4-chlorophenyl)(3-(2-hydroxyethyl)-5-methoxy-2-methyl-1H-indol-1-yl)methanone

Conditions
ConditionsYield
With borane-THF In tetrahydrofuran at 5℃; for 18h;98%
With dimethylsulfide borane complex In tetrahydrofuran at 20℃; for 22h; Cooling with ice;91%
With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere;90%
2,2,2,-trichloroethoxycarbonyl azide

2,2,2,-trichloroethoxycarbonyl azide

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

2,2,2-trichloroethyl-((1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-yl)methyl)carbamic acid ester

2,2,2-trichloroethyl-((1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-yl)methyl)carbamic acid ester

Conditions
ConditionsYield
With dmap; copper diacetate In acetonitrile at 80℃; for 0.25h; Schlenk technique; Sealed tube;98%
With dmap; copper diacetate In acetonitrile at 80℃; for 3h; Curtius Rearrangement; Inert atmosphere;93%
N-tert-butoxycarbonyl-O-diethylcarbamoyl-N-bromopropylhydroxylamine

N-tert-butoxycarbonyl-O-diethylcarbamoyl-N-bromopropylhydroxylamine

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

3-((tert-butoxycarbonyl)((diethylcarbamoyl)oxy)amino)propyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate

3-((tert-butoxycarbonyl)((diethylcarbamoyl)oxy)amino)propyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃;98%
ethanol
64-17-5

ethanol

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

indomethacin ethyl ester
16401-99-3

indomethacin ethyl ester

Conditions
ConditionsYield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 16h;97%
Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With oxalyl dichloride In dichloromethane at 20℃; for 2h;
Stage #2: ethanol With triethylamine In dichloromethane for 0.5h;
93%
With toluene-4-sulfonic acid In toluene at 140℃; for 6h; Dean-Stark;90%
(E)-hept-2-en-1-ol
33467-76-4

(E)-hept-2-en-1-ol

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid hept-2-enyl ester

[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid hept-2-enyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h; Esterification;97%
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

benzylamine
100-46-9

benzylamine

N-benzyl-2-[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetamide
572875-44-6

N-benzyl-2-[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetamide

Conditions
ConditionsYield
With zirconium(IV) chloride In tetrahydrofuran at 70℃; for 24h; Molecular sieve; Inert atmosphere;97%
With (2-iodo-4',5-dimethoxy-[1,1'-biphenyl]-3-yl)boronic acid In dichloromethane at 24 - 25℃; for 6h; Molecular sieve;94%
With (2-bromophenyl)boronic acid In dichloromethane at 25℃; for 48h; Molecular sieve;93%
With bis(cyclopentadienyl)titanium dichloride In tetrahydrofuran at 70℃; for 24h; Molecular sieve; Sealed tube; Inert atmosphere;85%
2-(Trimethylsilyl)ethanol
2916-68-9

2-(Trimethylsilyl)ethanol

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

2-(trimethylsilyl)ethyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate
1224508-94-4

2-(trimethylsilyl)ethyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 25℃; Inert atmosphere;97%
isopropyloxycarbonyloxymethyl iodide
258841-42-8

isopropyloxycarbonyloxymethyl iodide

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

[(1-methyl)ethoxycarbonyloxy]methyl 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indolylacetate
1268602-80-7

[(1-methyl)ethoxycarbonyloxy]methyl 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indolylacetate

Conditions
ConditionsYield
Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With N,N,N',N'-tetramethylguanidine In N,N-dimethyl acetamide at -15℃; Inert atmosphere;
Stage #2: isopropyloxycarbonyloxymethyl iodide In N,N-dimethyl acetamide at -15℃; Inert atmosphere;
96.6%
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetyl chloride
20357-37-3

1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetyl chloride

Conditions
ConditionsYield
With thionyl chloride In benzene at 65 - 70℃; for 1h;96.5%
With oxalyl dichloride In dichloromethane at 0 - 20℃; for 3.5h;96%
With oxalyl dichloride In dichloromethane at 20℃; for 8h; Inert atmosphere;96%
2-Butoxyethanol
111-76-2

2-Butoxyethanol

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 2-butoxy-ethyl ester

[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 2-butoxy-ethyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h; Esterification;96%
cyclohexylethan-1-ol
4442-79-9

cyclohexylethan-1-ol

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 2-cyclohexyl-ethyl ester

[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 2-cyclohexyl-ethyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h; Esterification;96%
3,3-dimethylbutanol
624-95-3

3,3-dimethylbutanol

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

3,3-dimethylbutyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate
1224508-90-0

3,3-dimethylbutyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate

Conditions
ConditionsYield
With 3-{[(ethylimino)methylene]-amino}-N,N,N-trimethyl-1-propanaminium iodide; dmap In dichloromethane at 0 - 20℃; Inert atmosphere;96%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 25℃; Inert atmosphere;96%
1-methylbutylzinc bromide

1-methylbutylzinc bromide

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

2-(5-methoxy-2-methyl-1-(4-(pentan-2-yl)benzoyl)-1H-indol-3-yl)acetic acid

2-(5-methoxy-2-methyl-1-(4-(pentan-2-yl)benzoyl)-1H-indol-3-yl)acetic acid

Conditions
ConditionsYield
Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With C40H55Cl5N3Pd In toluene at 0℃; for 0.0833333h; Negishi Coupling; Inert atmosphere; Cooling with ice;
Stage #2: 1-methylbutylzinc bromide In tetrahydrofuran; toluene at 23℃; for 2h; Inert atmosphere;
96%
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Cyclopropylamine
765-30-0

Cyclopropylamine

2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-N-cyclopropylacetamide

2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-N-cyclopropylacetamide

Conditions
ConditionsYield
Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran for 2h;
Stage #2: Cyclopropylamine In tetrahydrofuran at 20℃; for 2h;
96%
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

syringic aldehyde
134-96-3

syringic aldehyde

C28H24ClNO7

C28H24ClNO7

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; Steglich Esterification; Inert atmosphere;96%
8-Bromo-1-octene
2695-48-9

8-Bromo-1-octene

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

oct-7-en-1-yl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate

oct-7-en-1-yl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;96%
tert-Butyl chloroacetate
107-59-5

tert-Butyl chloroacetate

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

acemetacin tert-butyl ester
75302-98-6

acemetacin tert-butyl ester

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; sodium carbonate In toluene at 75℃; for 45h; Large scale;95.7%
iodomethyl pivaloate
53064-79-2

iodomethyl pivaloate

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

pivaloyloxymethyl 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indolylacetate
99199-42-5

pivaloyloxymethyl 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indolylacetate

Conditions
ConditionsYield
Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With N,N,N',N'-tetramethylguanidine In N,N-dimethyl acetamide at -10 - 20℃; Inert atmosphere;
Stage #2: iodomethyl pivaloate In N,N-dimethyl acetamide at -20 - -15℃;
95.5%
4-Fluorophenol
371-41-5

4-Fluorophenol

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 4-fluoro-phenyl ester

[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 4-fluoro-phenyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h; Esterification;95%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere;
2-phenylethanol
60-12-8

2-phenylethanol

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

phenethyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate
63170-54-7

phenethyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h; Esterification;95%
With C10H10Zr(2+)*2CF3O3S(1-)*C4H8O at 80℃; for 24h; Sealed tube;70%
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

2-(5-methoxy-2-methyl-1H-indol-3-yl)acetamide
15992-10-6

2-(5-methoxy-2-methyl-1H-indol-3-yl)acetamide

Conditions
ConditionsYield
Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With chloroformic acid ethyl ester
Stage #2: With ammonium hydroxide; sodium hydroxide
95%
Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With 4-methyl-morpholine; chloroformic acid ethyl ester In tetrahydrofuran at -10℃; for 0.5h;
Stage #2: With ammonium hydroxide In tetrahydrofuran at 20℃; for 3h;
Stage #3: With water; sodium hydroxide In tetrahydrofuran
88%
Multi-step reaction with 3 steps
1.1: 4-methyl-morpholine / tetrahydrofuran / 0.17 h / -10 °C
1.2: 0.5 h
2.1: ammonium hydroxide / tetrahydrofuran / 3 h / 20 °C
3.1: sodium hydroxide / tetrahydrofuran
View Scheme
O-<3-Hydroxypropyl>hydroxylamine
343925-76-8

O-<3-Hydroxypropyl>hydroxylamine

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methylindol-3-yl}-N-(3-hydroxypropoxy)acetamide

2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methylindol-3-yl}-N-(3-hydroxypropoxy)acetamide

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃;95%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃;95%

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