5-Acetamidoindole

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5-Acetamidoindole Basic information
Product Name:5-Acetamidoindole
Synonyms:Nsc74979;N-(1H-indol-5-yl)acetaMide;Acetamide, N-1H-indol-5-yl-;5-Acetamidoindole
CAS:7145-71-3
MF:C10H10N2O
MW:174.2
EINECS:604-604-1
Product Categories:
Mol File:7145-71-3.mol
5-Acetamidoindole Structure
5-Acetamidoindole Chemical Properties
Melting point 117-118 °C(Solv: acetonitrile (75-05-8))
Boiling point 461.2±18.0 °C(Predicted)
density 1.290±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
pka15.59±0.43(Predicted)
AppearanceWhite to off-white Solid
Safety Information
HS Code 2933998090
MSDS Information
5-Acetamidoindole Usage And Synthesis
Synthesis
5-Aminoindole

5192-03-0

Acetyl chloride

75-36-5

5-ACETAMIDOINDOLE

7145-71-3

General method (10): 5-Aminoindole (1.0 eq.) and triethylamine (3.6 eq.) were dissolved in dichloromethane (10 mL, corresponding to 1.182 mmol of raw material) and acetyl chloride (1.2 eq.) was added slowly. The reaction mixture was stirred at room temperature for 3 hours. After completion of the reaction, the mixture was poured into water and extracted three times with dichloromethane. The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by fast silica gel column chromatography using 7:3 hexane/ethyl acetate as eluent afforded 5-acetamidoindole (Intermediate 17A/-(1/-/-indol-5-yl)acetamide, Intermediate 17) as a clear oil (177 mg, 1.016 mmol, 85% yield).1H NMR (400 MHz, CDCl3) δ 8.27 ( bs, 1H), 7.80 (s, 1H), 7.30 (d, J = 8.5 Hz, 2H), 7.20 (dd, J = 8.8, 2.0 Hz, 2H), 6.50 (s, 1H), 2.18 (s, 3H).

References[1] Patent: WO2016/200339, 2016, A1. Location in patent: Page/Page column 93-94
[2] European Journal of Medicinal Chemistry, 2018, vol. 156, p. 344 - 367
5-Acetamidoindole Preparation Products And Raw materials
Raw materials5-Aminoindole-->Acetyl chloride-->Triethylamine-->Dichloromethane
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