7145-71-3

Basic information

• Product Name: 5-ACETAMIDOINDOLE
• Synonyms: 5-ACETAMIDOINDOLE;Nsc74979;N-(1H-indol-5-yl)acetaMide
• CAS NO: 7145-71-3
• Molecular Formula: C₁₀H₁₀N₂O
• Molecular Weight: 174.2
• EINECS: 604-604-1
• Mol File: 7145-71-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 461.2 °C at 760 mmHg
• Flash Point: 232.7 °C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 1.09E-08mmHg at 25°C
• Refractive Index: 1.711
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 5-ACETAMIDOINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-ACETAMIDOINDOLE(7145-71-3)
• EPA Substance Registry System: 5-ACETAMIDOINDOLE(7145-71-3)

Safety Data

• Hazardous Substances Data: 7145-71-3(Hazardous Substances Data)

Usage

General Description

5-Acetamidoindole is a chemical compound with the molecular formula C10H10N2O. It is a derivative of indole and has a secondary amide group attached to the carbon at position 5 of the indole ring. 5-ACETAMIDOINDOLE is commonly used in organic synthesis and medicinal chemistry as a building block for the preparation of various biologically active molecules. It has also been studied for its potential pharmacological properties, including its role as an inhibitor of certain enzymes and as a potential anti-cancer agent. Additionally, 5-acetamidoindole has been investigated for its photophysical and photochemical properties, making it a versatile molecule with multiple potential applications in various scientific fields.

InChI:InChI=1/C10H10N2O/c1-7(13)12-9-2-3-10-8(6-9)4-5-11-10/h2-6,11H,1H3,(H,12,13)

Synthetic route

tungsten hexacarbonyl (14040-11-0) + 5-nitroindole (6146-52-7) + carbonic acid dimethyl ester (616-38-6) → N-(1H-indol-5-yl)acetamide (7145-71-3)

Conditions	Yield
With di(rhodium)tetracarbonyl dichloride; 1,3-bis-(diphenylphosphino)propane; sodium phosphate; sodium iodide In water at 120℃; for 24h; Inert atmosphere; Sealed tube;	92%

5-amino-1H-indole (5192-03-0) + acetyl chloride (75-36-5) → N-(1H-indol-5-yl)acetamide (7145-71-3)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h;	85%
With triethylamine In dichloromethane at 20℃; for 3h;	85%

5-nitroindole (6146-52-7) → N-(1H-indol-5-yl)acetamide (7145-71-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / ethanol / 2.5 h / 1551.49 Torr 2: triethylamine / dichloromethane / 3 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / ethanol / 2.5 h / 1551.49 Torr 2: triethylamine / dichloromethane / 3 h / 20 °C View Scheme

N-(1H-indol-5-yl)acetamide (7145-71-3) → N,N’-(2-(5-acetamido-1H-indol-3-yl)-3-oxo-2,3’-biindoline-5,5’-diyl)diacetamide (1414941-83-5)

Conditions	Yield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; benzoic acid In acetonitrile at 65℃; for 72h;	93%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; benzoic acid; copper dichloride In acetonitrile at 60℃; for 6h; regioselective reaction;	93%
With pyridine; methanesulfonic acid; sodium nitrite at 20℃;	91%

3,3,3-trifluoro-2-phenylpropene (384-64-5) + N-(1H-indol-5-yl)acetamide (7145-71-3) → (Z)-N,N'-((1-fluoro-2-phenylprop-1-ene-1,3-diyl)bis(1H-indole-1,5-diyl))diacetamide

Conditions	Yield
With sodium t-butanolate In N,N-dimethyl-formamide at -5℃; for 0.166667h; Schlenk technique;	86%

N-(1H-indol-5-yl)acetamide (7145-71-3) → (E)-N,N'-(3-(hydroxyimino)-2,3'-bi(3H-indole)-5,5'-diyl)diacetamide (1448161-67-8)

Conditions	Yield
With sodium nitrite In pyridine at 20℃; for 10h; Green chemistry; regioselective reaction;	85%
With iron(III) chloride hexahydrate; sodium nitrite In acetonitrile at 25℃;

1-Methyl-4-piperidone (1445-73-4) + N-(1H-indol-5-yl)acetamide (7145-71-3) → 5-(acetyl)amino-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Conditions	Yield
With sodium methylate In methanol for 48h; Heating;	56%

N-(1H-indol-5-yl)acetamide (7145-71-3) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → N-(3-formyl-1H-indol-5-yl)acetamide (91137-92-7)

Conditions	Yield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate for 0.333333h; Vilsmeier-Haack Formylation; Cooling with ice; Stage #2: N-(1H-indol-5-yl)acetamide at 20℃; for 1.5h; Vilsmeier-Haack Formylation;	52%

1-propyl-4-piperidone (23133-37-1) + N-(1H-indol-5-yl)acetamide (7145-71-3) → N-[3-(1-Propyl-1,2,3,6-tetrahydro-pyridin-4-yl)-1H-indol-5-yl]-acetamide

Conditions	Yield
With sodium methylate In methanol for 48h; Heating;	44%

Upstream product

• 5192-03-0 5-amino-1H-indole 
• 75-36-5 acetyl chloride 
• 6146-52-7 5-nitroindole 
• 14040-11-0 tungsten hexacarbonyl 
• 616-38-6 carbonic acid dimethyl ester 

Relevant articles and documents

Method for promoting acylation of amine or alcohol by carbon dioxide

The invention relates to a method for promoting acylation of amine or alcohol by carbon dioxide, which comprises the following steps of: mixing an amine compound, carboxylate or thiocarboxylate compound and a reaction solvent under the action of carbon dioxide, and reacting to obtain an amide compound, or under the action of carbon dioxide, mixing the alcohol compound, the thiocarboxylate compound and the reaction solvent [gamma]-valerolactone, and reacting to obtain the ester compound. According to the invention, under the promotion action of carbon dioxide, carboxylate or thiocarboxylate is used as an acylation reagent, and amine and alcohol are converted into amide and ester compounds in the absence of a transition metal catalyst, so that acylation reagents such as acyl chloride or anhydride with irritation and corrosivity are avoided; and the method has the advantages of simple operation, mild reaction conditions, high tolerance of substrate functional groups, strong applicability and high yield, and provides an efficient, reliable and economical preparation method for synthesis of amide and ester compounds.

Discovery of the cancer cell selective dual acting anti-cancer agent (Z)-2-(1H-indol-3-yl)-3-(isoquinolin-5-yl)acrylonitrile (A131)

Selective targeting of cancer cells over normal cells is a key objective of targeted therapy. However few approaches achieve true mechanistic selectivity resulting in debilitating side effects and dose limitation. In this work we describe the discovery of A131 (4a), a new agent with an unprecedented dual mechanism of action targeting both mitosis and autophagy. Compound 4a was first identified in a phenotypic screen in which HeLa cells treated with 4a manifested mitotic arrest along with formation of multiple vesicles. Further investigations showed that 4a causes an increase in mitotic marker pH3 and autophagy marker LC3. Importantly 4a induces cell death in cancer cells while sparing normal cells which regrow after 4a is removed. Dual activities against pH3 and LC3 markers are required for cancer cell selectivity. An extensive SAR investigation confirmed 4a as the optimal dual inhibitor with potency against a panel of 30 cancer cell lines (average antiproliferative GI50 1.5 μM). In a mouse model of paclitaxel-resistant colon cancer, 4a showed 74% tumor growth inhibition when administered at a dose of 20 mg/kg IP twice a day.