608-05-9

Basic information

• Product Name: 5-Methylisatin
• Synonyms: AURORA 1898;BUTTPARK 34\07-89;IFLAB-BB F0266-0774;5-METHYL-1H-INDOLE-2,3-DIONE;5-METHYLISATIN;5-METHYLINDOLE-2,3-DIONE;AKOS BBS-00000995;AKOS AU36-M121
• CAS NO: 608-05-9
• Molecular Formula: C₉H₇NO₂
• Molecular Weight: 161.16
• EINECS: 210-152-1
• Product Categories: Indane/Indanone and Derivatives;Indoles;Simple Indoles;Building Blocks;C7 to C9;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 608-05-9.mol
• Article Data: 81

Chemical Properties

• Melting Point: 180 °C (dec.)(lit.)
• Appearance: orange/crystalline
• Density: 1.301 g/cm³
• Refractive Index: 1.598
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: methanol: soluble25mg/mL, clear to slightly hazy, orange to red
• PKA: 10.42±0.20(Predicted)
• BRN: 123738
• CAS DataBase Reference: 5-Methylisatin(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methylisatin(608-05-9)
• EPA Substance Registry System: 5-Methylisatin(608-05-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• RTECS: NL7939300
• HazardClass: IRRITANT
• Hazardous Substances Data: 608-05-9(Hazardous Substances Data)

Usage

Chemical Properties

Red to brown powder or crystals

Uses

Different sources of media describe the Uses of 608-05-9 differently. You can refer to the following data:
1. Reactant for preparation of:Antimycobacterial agentsPromoters of central nervous system (CNS) depression in miceInhibitors of TAK1 kinaseAnti-human immunodeficiency virus (HIV) agentPotent herpes simplex virus (HSV) inhibitorsAntimicrobial agentsIKKβ inhibitorsPotential drug to combat human immunodeficiency virus-tuberculosis (HIV-TB) coinfectionCyclooxygenase 1/2 (COX-1/2) and 5-lipoxygenase (5-LOX) inhibitorsAntibacterial and anticancer agents
2. Reactant for preparation of:? ;Antimycobacterial agents1? ;Promoters of central nervous system (CNS) depression in mice2? ;Inhibitors of TAK1 kinase3? ;Anti-human immunodeficiency virus (HIV) agent4? ;Potent herpes simplex virus (HSV) inhibitors5? ;Antimicrobial agents6? ;IKKβ inhibitors7? ;Potential drug to combat human immunodeficiency virus-tuberculosis (HIV-TB) coinfection8? ;Cyclooxygenase 1/2 (COX-1/2) and 5-lipoxygenase (5-LOX) inhibitors9? ;Antibacterial and anticancer agents

General Description

5-Methylisatin is an inhibitor of atrial natriuretic peptide (ANP) receptor coupled with guanylyl cyclase (GC).

InChI:InChI=1/C9H7NO2/c1-5-2-3-7-6(4-5)8(11)9(12)10-7/h2-4H,1H3,(H,10,11,12)

Synthetic route

2-Diethylamino-5-methyl-indol-3-on → 5-methyl-indole-2,3-dione (608-05-9)

Conditions	Yield
With hydrogenchloride In ethanol	100%

2-(2-amino-5-methylphenyl)-N-hexyl-2-oxoacetamide → 5-methyl-indole-2,3-dione (608-05-9)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water at 20℃;	99%

2-hydroxyimino-N-p-tolyl-acetamide (1132-40-7) → 5-methyl-indole-2,3-dione (608-05-9)

Conditions	Yield
With sulfuric acid at 20 - 30℃; for 1.66667h;	97.3%
Stage #1: 2-hydroxyimino-N-p-tolyl-acetamide With sulfuric acid at 60 - 80℃; Stage #2: With water for 0.5h; Cooling with ice;	86.9%
Stage #1: 2-hydroxyimino-N-p-tolyl-acetamide With sulfuric acid at 20℃; Sandmeyer reaction; Stage #2: With water Cooling with ice;	85%

N-tert-butyl-(2-amino-5-methyl-phenyl)-glyoxylamide → 5-methyl-indole-2,3-dione (608-05-9)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 5h;	92.7%

5-methylindolin-2-one (3484-35-3) → 5-methyl-indole-2,3-dione (608-05-9)

Conditions	Yield
With oxygen; sodium iodide In tetrahydrofuran at 60℃; for 12h; Schlenk technique; chemoselective reaction;	92%
Multi-step reaction with 2 steps 1: CuBr2 / ethyl acetate / 80 °C 2: water / methanol / 2 h / Heating View Scheme
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; oxygen In acetonitrile at 20℃; for 18h;

5-methyl-2,3-dihydro-1H-indole (65826-95-1) → 5-methyl-indole-2,3-dione (608-05-9)

Conditions	Yield
With iodine pentoxide In dimethyl sulfoxide at 80℃;	88%
With o-iodosobenzoic acid; oxygen In dimethyl sulfoxide at 80℃; for 12h; Green chemistry;	83%

(Z)-2-(hydroxylimino)-N-p-tolylacetamide (1233474-66-2) → 5-methyl-indole-2,3-dione (608-05-9)

Conditions	Yield
With sulfuric acid at 50 - 80℃;	86.9%

5-methyl-1H-indole (614-96-0) → 5-methyl-indole-2,3-dione (608-05-9)

Conditions	Yield
With oxygen; Rose Bengal lactone In water; N,N-dimethyl-formamide for 18h; Inert atmosphere; Irradiation;	86%
With N-iodo-succinimide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 15 - 25℃; for 4h;	83%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; oxygen In acetonitrile at 20℃; for 11h;	82%
With tert.-butylhydroperoxide; iodine In dimethyl sulfoxide at 80℃; for 24h;	64%

C10H7N3O2 → 5-methyl-indole-2,3-dione (608-05-9)

Conditions	Yield
With copper(I) bromide In water; benzonitrile at 140℃; for 4h; Inert atmosphere;	86%

chloral hydrate (302-17-0) + p-toluidine (106-49-0) → 5-methyl-indole-2,3-dione (608-05-9)

Conditions	Yield
Stage #1: chloral hydrate; p-toluidine With sulfuric acid; hydroxylamine hydrochloride; sodium sulfate In water at 130℃; for 0.5h; Stage #2: With sulfuric acid at 50 - 70℃; for 1h;	80%
With hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate In water at 90℃; for 0.0833333h;	66.3%
Stage #1: chloral hydrate; p-toluidine With hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate In water Stage #2: With sulfuric acid at 60 - 80℃;	56%

5-methylindole-3-carboxaldehyde (52562-50-2) → 5-methyl-indole-2,3-dione (608-05-9)

Conditions	Yield
With sodium chloride In water; acetonitrile at 50℃; for 2h; Green chemistry;	80%

oxalyl dichloride (79-37-8) + p-toluidine (106-49-0) → 5-methyl-indole-2,3-dione (608-05-9)

Conditions	Yield
With H-β zeolite In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere;	76%

carbon monoxide (201230-82-2) + N'-(2-Bromo-4-methylphenyl)-N,N-dimethylurea (58226-34-9) → 5-methyl-indole-2,3-dione (608-05-9)

Conditions	Yield
Stage #1: N'-(2-Bromo-4-methylphenyl)-N,N-dimethylurea With methyllithium In tetrahydrofuran; diethyl ether at 0℃; Stage #2: With tert.-butyl lithium In tetrahydrofuran; diethyl ether; n-heptane at 0℃; for 1h; Stage #3: carbon monoxide In tetrahydrofuran; diethyl ether; n-heptane at 0℃; for 0.5h;	72%
Yield given; Multistep reaction;

3-(p-tolylimino)-5-methyl-N-p-tolyl-3H-indole-2-amine (29650-23-5) → 5-methyl-indole-2,3-dione (608-05-9)

Conditions	Yield
With hydrogenchloride; acetic acid In water for 0.333333h; Reflux;	68%

5-methylisatin-3-oxime (13208-98-5) + triisopropyl phosphite (116-17-6) → 5-methyl-indole-2,3-dione (608-05-9) + (3-Hydroxy-5-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl)-phosphonic acid diisopropyl ester + (3-Hydroxyamino-5-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl)-phosphonic acid diisopropyl ester

Conditions	Yield
With acetic acid at 100℃; for 12h;	A n/a B n/a C 60%

5-methylisatin-3-oxime (13208-98-5) + triethyl phosphite (122-52-1) → 5-methyl-indole-2,3-dione (608-05-9) + diethyl 3-hydroxy-5-methyl-2-oxoindolin-3-ylphosphonate + (3-Hydroxyamino-5-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl)-phosphonic acid diethyl ester

Conditions	Yield
With acetic acid at 100℃; for 12h;	A n/a B n/a C 60%

Glyoxal (131543-46-9) + p-toluidine (106-49-0) → 5-methyl-indole-2,3-dione (608-05-9)

Conditions	Yield
With copper(II) choride dihydrate; caesium carbonate; trifluoroacetic acid In 2-methyltetrahydrofuran; water at 70℃; for 5h; Schlenk technique; Inert atmosphere;	47%

oxalyl dichloride (79-37-8) + p-toluidine hydrochloride (540-23-8) → 5-methyl-indole-2,3-dione (608-05-9)

Conditions	Yield
With nitrobenzene Erwaermen des Reaktionsgemisches mit Aluminiumchlorid;

5-methyl-2-nitrobenzaldehyde (5858-28-6) → 5-methyl-indole-2,3-dione (608-05-9)

Conditions	Yield
With acetone Man oxydiert das (nicht isolierte) <6-Nitro-α-oxy-3-methyl-benzyl>-aceton mit Kaliumpermanganat in sodaalkalischer Loesung bei 60-70grad;

2-hydroxyimino-N-p-tolyl-acetamide (1132-40-7) → 5-methyl-indole-2,3-dione (608-05-9) + p-tolyl-oxalamide (42868-90-6)

Conditions	Yield
With PPA

N,N'-bis(4-methylphenyl)ethanediimidoyl dichloride (7472-70-0) → 5-methyl-indole-2,3-dione (608-05-9)

Conditions	Yield
With sulfuric acid
With sulfuric acid

di-p-toluidino-acetic acid ethyl ester (861524-16-5) → 5-methyl-indole-2,3-dione (608-05-9)

Conditions	Yield
With mineral acid

ethanol (64-17-5) + 2-methoxy-5-methyl-indolin-3-one (861586-94-9) → 5-methyl-indole-2,3-dione (608-05-9)

5-methylisatin-3-oxime (13208-98-5) + phosphorous acid trimethyl ester (121-45-9) → 5-methyl-indole-2,3-dione (608-05-9) + dimethyl 3-hydroxy-5-methyl-2-oxoindolin-3-ylphosphonate

Conditions	Yield
With acetic acid at 100℃; for 12h;

5-methylisatin-3-oxime (13208-98-5) + phosphorous acid trimethyl ester (121-45-9) → 5-methyl-indole-2,3-dione (608-05-9) + dimethyl 3-hydroxy-5-methyl-2-oxoindolin-3-ylphosphonate + (3-Hydroxyamino-5-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl)-phosphonic acid dimethyl ester

Conditions	Yield
With acetic acid at 100℃; for 12h;

1-p-toluenesulfonyl-5-methyl-isatin → 5-methyl-indole-2,3-dione (608-05-9)

Conditions	Yield
With sulfuric acid Darstellung;

sulfuric acid (7664-93-9) + 5-methyl-1-tosylindoline-2,3-dione (99448-78-9) → 5-methyl-indole-2,3-dione (608-05-9)

5-methyl-isatin-p-tolylimide-(3) → 5-methyl-indole-2,3-dione (608-05-9)

Conditions	Yield
With hydrogenchloride
With hydrogenchloride

3-imino-5-methyl indolin-2-one + acid → 5-methyl-indole-2,3-dione (608-05-9)

5-methyl-indole-2,3-dione (608-05-9) → 7-bromo-5-methyl-2,3-dihydro-1H-indole-2,3-dione (108938-16-5)

Conditions	Yield
With N-Bromosuccinimide at 20℃; for 24h;	100%
With water; bromine
With chloroform; bromine
With bromine In acetic acid

5-methyl-indole-2,3-dione (608-05-9) + 2-oxo-propionic acid (127-17-3) → 6-methylquinoline-2,4-dicarboxylic acid (91493-56-0)

Conditions	Yield
Stage #1: 5-methyl-indole-2,3-dione; 2-oxo-propionic acid With potassium hydroxide In water at 40℃; for 12h; Stage #2: With hydrogenchloride In water pH=3;	100%
With potassium hydroxide In water at 40℃; for 12h;	100%
With potassium hydroxide In water at 40℃; for 16h; Pfitzinger Quinoline Synthesis;	96%

5-methyl-indole-2,3-dione (608-05-9) + -CH(CH3)2 halide → 1-isopropyl-5-methylindoline-2,3-dione (620931-09-1)

Conditions	Yield
With caesium carbonate In acetonitrile at 20℃;	100%

5-methyl-indole-2,3-dione (608-05-9) + -CH2CH2CH3 halide → 5-methyl-1-propylindoline-2,3-dione (63725-87-1)

Conditions	Yield
With caesium carbonate In acetonitrile at 20℃;	100%

5-methyl-indole-2,3-dione (608-05-9) + -CH2CH3 halide → 1-ethyl-5-methyl-2,3-indolinedione (299925-63-6)

Conditions	Yield
With caesium carbonate In acetonitrile at 20℃;	100%

5-methyl-indole-2,3-dione (608-05-9) + -CH3 halide → 1,5-dimethyl-1H-indole-2,3-dione (66440-60-6)

Conditions	Yield
With caesium carbonate In acetonitrile at 20℃;	100%

5-methyl-indole-2,3-dione (608-05-9) + N-(2-bromophenyl)hydrazinecarbothioamide (25688-12-4) → 5-methyl-1H-indole-2,3-dione 3-[N-(2-bromophenyl)thiosemicarbazone] (1084892-90-9)

Conditions	Yield
With sulfuric acid In ethanol for 5h; Reflux;	99%

5-methyl-indole-2,3-dione (608-05-9) + 1-bromo-hexane (111-25-1) → 1-hexyl-5-methylindoline-2,3-dione (620931-14-8)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 140℃; Microwave irradiation;	99%

5-methyl-indole-2,3-dione (608-05-9) + nitromethane (75-52-5) → 3-hydroxy-5-methyl-3-(nitromethyl)-2,3-dihydro-1H-indol-2-one (1315258-63-9)

Conditions	Yield
With (3ξ,8α,9R)-cinchonan-6',9-diol; benzoic acid In N,N-dimethyl acetamide at -15℃; for 3h; Henry reaction; optical yield given as %ee; enantioselective reaction;	99%
With 9-O-benzyl-6'-hydroxycinchonidine In tetrahydrofuran at -30℃; for 120h; Henry reaction; optical yield given as %ee; enantioselective reaction;	92%
In tetrahydrofuran at -10℃; for 11h; Henry reaction; optical yield given as %ee; enantioselective reaction;	88%

5-methyl-indole-2,3-dione (608-05-9) + aminomalonic acid diethyl ester (6829-40-9) + dimethyl acetylenedicarboxylate (762-42-5) → 5',5'-diethyl 3',4'-dimethyl 5-methyl-2-oxospiro[indoline-3,2'-pyrrole]-3',4',5',5'(1'H)-tetracarboxylate (1459805-65-2)

Conditions	Yield
With trifluoroacetic acid In 1,2-dichloro-ethane at 60℃; for 36h; Time; Molecular sieve;	99%

5-methyl-indole-2,3-dione (608-05-9) + 3-amino-1-phenyl-2-pyrazolin-5-one (4149-06-8) + 6-methoxy-3,4-dihydro-1(2H)-naphthalenone (1078-19-9) → 3-methoxy-5'-methyl-9-phenyl-6,9,10,11-tetrahydrospiro[benzo[h]pyrazolo[3,4-b]quinoline-7,3'-indoline]-2',8(5H)-dione

Conditions	Yield
With acetic acid In water at 90℃; for 7h; Green chemistry;	99%

5-methyl-indole-2,3-dione (608-05-9) + 2,2-difluoro-2-(3-methyl-4-nitro-1,2-oxazol-5-yl)-1-phenylethan-1-one → 3-(difluoro(3-methyl-4-nitroisoxazol-5-yl)methyl)-3-hydroxy-5-methylindolin-2-one

Conditions	Yield
With methanol; triethylamine at 20℃; for 24h;	99%

5-methyl-indole-2,3-dione (608-05-9) + Dimethyl phosphite (868-85-9) → dimethyl 3-hydroxy-5-methyl-2-oxoindolin-3-ylphosphonate

Conditions	Yield
With phosphotungstic acid supported on silica-coated magnetic Fe3O4 nanoparticle In neat (no solvent) at 80℃; for 16h; Kabachnik-Fields Reaction; Green chemistry;	98%
With magnetic nanoparticle γ-Fe2O3-immobilized 1,5,7-triazabicyclo[4.4.0]dec-5-ene In neat (no solvent) at 60℃; for 5h;	91%
at 100℃; for 6h;	80%
With β‐cyclodextrin In methanol; water at 20℃;

5-methyl-indole-2,3-dione (608-05-9) + phosphonic acid diethyl ester (762-04-9) → diethyl 3-hydroxy-5-methyl-2-oxoindolin-3-ylphosphonate

Conditions	Yield
With phosphotungstic acid supported on silica-coated magnetic Fe3O4 nanoparticle In neat (no solvent) at 80℃; for 16h; Kabachnik-Fields Reaction; Green chemistry;	98%
With zinc(II) oxide In neat (no solvent) at 20℃; for 0.666667h;	94%
With magnetic nanoparticle γ-Fe2O3-immobilized 1,5,7-triazabicyclo[4.4.0]dec-5-ene In neat (no solvent) at 60℃; for 6h;	91%
at 100℃; for 6h;	80%
With β‐cyclodextrin In methanol; water at 20℃;

5-methyl-indole-2,3-dione (608-05-9) + 4-methoxy-aniline (104-94-9) → 3-(4-methoxy-phenylimino)-5-methyl-1,3-dihydro-indol-2-one

Conditions	Yield
In water at 20℃; for 4h;	98%
In ethanol Heating;	72%
With acetic acid In ethanol for 0.75h; Reflux;
With acetic acid at 20℃; for 2h;
In ethanol for 2h; Reflux;

indole (120-72-9) + 5-methyl-indole-2,3-dione (608-05-9) → 5'-methyl-1H,1''H-3,3':3',3''-terindol-2'(1'H)-one

Conditions	Yield
With 60 wtpercent phosphotungstic acid supported on MCM-41 In tetrahydrofuran at 20℃; for 2.5h; Friedel-Crafts Acylation;	98%
With 1‐(2‐hydroxyethyl)‐1,4‐diazabicyclo[2.2.2]octanylium tetrachloroferrate In ethanol at 50℃; for 0.0833333h; Green chemistry;	98%
With boron trifluoride supported on nano-SiO2 In methanol for 0.45h; Reflux;	95%

2-{[5-(4-methoxyphenyl)-1,3,5-oxadiazol-2-yl]imino}-4-thiazolidinone (89335-21-7) + 5-methyl-indole-2,3-dione (608-05-9) → 3-[2-[(E)-5-(4-Methoxy-phenyl)-[1,3,4]oxadiazol-2-ylimino]-4-oxo-thiazolidin-(5Z)-ylidene]-5-methyl-1,3-dihydro-indol-2-one

Conditions	Yield
With sodium acetate; acetic anhydride In acetic acid at 150 - 160℃; for 5h;	98%

2-Amino-6-((E)-nonadec-10-enyl)-benzoic acid (934273-34-4) + 5-methyl-indole-2,3-dione (608-05-9) → C35H48N2O3

Conditions	Yield
for 0.0666667h; microwave irradiation;	98%

5-methyl-indole-2,3-dione (608-05-9) + ethane-1,2-dithiol (540-63-6) → 5'-methylspiro[[1,3]dithiolane-2,3'-indolin]-2'-one

Conditions	Yield
With boron trifluoride diethyl etherate In acetic acid at 20 - 60℃; for 0.75h;	98%
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 16h;	62%
With boron trifluoride diethyl etherate; acetic acid at 60℃;

5-methyl-indole-2,3-dione (608-05-9) + 2-Hydroxy-1,4-naphthoquinone (83-72-7) + malononitrile (109-77-3) → 2-amino-5'-methyl-2',5,10-trioxo-5,10-dihydrospiro[benzo[g]chromene-4,3'-indoline]-3-carbonitrile (1204748-04-8)

Conditions	Yield
With toluene-4-sulfonic acid In water for 3h; Reflux;	98%
With graphene oxide-supported dicationic ionic liquid In water for 0.333333h; Reflux; Green chemistry;	95%

5-methyl-indole-2,3-dione (608-05-9) + edaravone (89-25-8) + malononitrile (109-77-3) → 6'-amino-3',5'-dimethyl-2-oxo-1'-phenyl-1'H-spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile (380432-38-2)

Conditions	Yield
With sodium chloride In water at 20℃; for 0.166667h; Sonication;	98%
With ammonium cerium (IV) nitrate In water at 20℃; for 0.166667h; Sonication; Green chemistry;	98%
With ZnS nanoparticles In water at 20℃; for 0.2h; ultrasonic irradiation;	97%
In water at 60℃; for 1h;	92%
With silica immobilized propyl imidazolium chloride In water for 0.5h; Reflux;	88%

5-methyl-indole-2,3-dione (608-05-9) + 4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one (83-07-8) + 2-mercaptopropanoic acid (79-42-5) → 3'-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)-5,5'-dimethyl-spiro[3H-indole-3,2'-thiazolidine]-2,4'(1H)-dione

Conditions	Yield
With cetyltrimethylammonim bromide In water Sonication; Combinatorial reaction / High throughput screening (HTS);	98%

5-methyl-indole-2,3-dione (608-05-9) + 2-methyl-3-bromo-1-propene (1458-98-6) → 3-(2-methylallyl)-3-hydroxy-5-methyl-1,3-dihydro-2H-indol-2-one (1342300-25-7)

Conditions	Yield
With indium In decaethylene glycol at 20℃; for 0.25h; Barbier reaction;	98%

5-methyl-indole-2,3-dione (608-05-9) + allyl bromide (106-95-6) → 3-allyl-3-hydroxy-5-methyl-1,3-dihydro-2H-indol-2-one (1309578-03-7)

Conditions	Yield
With indium In decaethylene glycol at 20℃; for 0.166667h; Barbier reaction;	98%

1,3-benzothiazol-6-amine (533-30-2) + 5-methyl-indole-2,3-dione (608-05-9) → 3-(benzothiazol-6-ylimino)-1,3-dihydro-5-methyl-2H-indole-2-one (1391950-07-4)

Conditions	Yield
In water at 20℃; for 3h;	98%

5-methyl-indole-2,3-dione (608-05-9) + 3-phenyl-1-(1H-pyrazol-1-yl)but-3-en-1-one → (S)-5-methyl-4'-phenylspiro[indoline-3,2'-pyran]-2,6'(3'H)-dione

Conditions	Yield
With 1-[3,5-bis(trifluoromethyl)phenyl]-3-[(1S,2S)-2-(dimethylamino)cyclohexyl]thiourea In acetonitrile at 25℃; for 24h; enantioselective reaction;	98%

5-methyl-indole-2,3-dione (608-05-9) + ethyl acetoacetate (141-97-9) → 3,3-bis(3-hydroxy-5-methyl-1H-pyrazol-4-yl)-5-methylindolin-2-one

Conditions	Yield
Stage #1: ethyl acetoacetate With hydrazine hydrate for 0.0833333h; Stage #2: 5-methyl-indole-2,3-dione With sodium hydrogencarbonate In ethanol at 78℃; for 18h;	98%

5-methyl-indole-2,3-dione (608-05-9) + 3-amino-1-phenyl-2-pyrazolin-5-one (4149-06-8) + inden-1-one (83-33-0) → 5'-methyl-2-phenyl-1,2,5,10-tetrahydro-3H-spiro[indeno[1,2-b]pyrazolo[4,3-e]pyridine-4,3'-indoline]-2',3-dione

Conditions	Yield
With acetic acid In water at 90℃; for 7h; Green chemistry;	98%

Upstream product

• 201230-82-2 carbon monoxide 
• 58226-34-9 N'-(2-Bromo-4-methylphenyl)-N,N-dimethylurea 
• 7664-93-9 sulfuric acid 
• 99448-78-9 5-methyl-1-tosylindoline-2,3-dione 
• 7647-01-0 hydrogenchloride 
• 16851-98-2 5-methyl-3-p-tolylimino-indolin-2-one 
• 861359-80-0 3,3'-dihydroxy-5-methyl-1,3,1',3'-tetrahydro-[3,3']biindolyl-2,2'-dione 
• 1132-40-7 2-hydroxyimino-N-p-tolyl-acetamide 
• 7472-70-0 N,N'-bis(4-methylphenyl)ethanediimidoyl dichloride 
• 861524-16-5 di-p-toluidino-acetic acid ethyl ester 
• 29650-23-5 3-(p-tolylimino)-5-methyl-N-p-tolyl-3H-indole-2-amine 
• 614-96-0 5-methyl-1H-indole 
• 29289-13-2 2-iodo-4-methylaniline 
• 131543-46-9 Glyoxal 

Downstream Products

• 199728-36-4 6-Methyl-2-(1-methyl-1H-imidazol-2-yl)-quinoline-4-carboxylic acid 
• 3484-35-3 5-methylindolin-2-one 
• 219660-85-2 5-methyl-3-[(3-phenyl-[1,8]naphthyridin-2-yl)-hydrazono]-1,3-dihydro-indol-2-one 
• 153465-48-6 2-(2-carboxyphenyl)-6-methyl-4-quinoline-carboxylic acid 
• 16851-98-2 3-(4-methyl-phenylimino)-5-methyl-1,3-dihydro-indol-2-one 
• 66440-24-2 3-(4-bromo-phenylimino)-5-methyl-1,3-dihydro-indol-2-one 
• 436089-38-2 3,6-dimethyl-2-phenylquinoline-4-carboxylic acid 
• 7364-26-3 5-Methyl-3-indazolone 
• 1201-24-7 5-methyl-1H-indazole-3-carboxylic acid 
• 28864-72-4 5-methyl-3-phenyl-3-hydroxy-1,3-dihydro-indol-2-one 
• 848941-28-6 (2-oxo-3-phenyl-2H-[1,8]naphthyridin-1-yl)-acetic acid (5-methyl-2-oxo-1,2-dihydro-indol-3-ylidene)-hydrazide 

Relevant articles and documents

Study on synthesis of some substituted N-propargyl isatins by propargylation reaction of corresponding isatins using potassium carbonate as base under ultrasound- and microwave-assisted conditions

Substituted N-propargyl isatins were synthesized by SN2 reaction of corresponding substituted isatins with propargyl bromide in the presence of anhydrous K2CO3 as base. We reported about study on systematically synthesis of these compounds using heating procedures under different reaction conditions, including microwave-assisted heating conditions at power of 100?W (Procedure A), conventional heating conditions in water bath at 50?°C in acetonitrile (Procedure B), and conventional heating conditions in water bath at 50?°C in DMF (procedure C). The best procedure A was deduced based on the investigations on the reaction conditions. Almost all substituted N-propargyl isatins were new, except compounds with R of H, 5-Me, 5-Cl and 5-Br substituents. The structures of the obtained compounds were confirmed by the modern spectroscopic methods.

Bicyclic heteroaryl compound with PAR4 antagonistic activity and application thereof

The invention discloses a bicyclic heteroaryl compound with PAR4 antagonistic activity and application thereof. The invention provides the bicyclic heteroaryl compound with PAR4 antagonistic activity,and the bicyclic heteroaryl compound has remarkable antagonistic activity on PAR4 in an in-vitro anti-platelet aggregation experiment, so that platelet aggregation is effectively inhibited, and the bicyclic heteroaryl compound can be used for preparing medicines for preventing or treating various thromboembolic diseases.

Visible-Light-Mediated Dearomatisation of Indoles and Pyrroles to Pharmaceuticals and Pesticides

Dearomatisation of indole derivatives to the corresponding isatin derivatives has been achieved with the aid of visible light and oxygen. It should be noted that isatin derivatives are highly important for the synthesis of pharmaceuticals and bioactive compounds. Notably, this chemistry works excellently with N-protected and protection-free indoles. Additionally, this methodology can also be applied to dearomatise pyrrole derivatives to generate cyclic imides in a single step. Later this methodology was applied for the synthesis of four pharmaceuticals and a pesticide called dianthalexin B. Detailed mechanistic studies revealed the actual role of oxygen and photocatalyst.