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17716-91-5

2-CHLORO-1-(1-METHYL-1H-INDOL-3-YL)-ETHANONE synthesis

4synthesis methods
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Yield:17716-91-5 53%

Reaction Conditions:

Stage #1: chloroacetonitrilewith phenylborondichloride in dichloromethane at 20; for 0.25 h;Inert atmosphere;
Stage #2: 1-methylindole in dichloromethane; for 1 h;Inert atmosphere;
Stage #3: with water;sodium carbonateInert atmosphere;

Steps:

General Procedure for Synthesizing 3-Acylindole Compounds (Exemplified by 3aa)

General procedure: A 1.5 mL (1.5 mmol) ofPhBCl2 (1.0 mol/L in CH2Cl2) was added to CH2Cl2 solution(4 mL) of the nitrile (5a) (173 mg, 1.2 mmol) at room temperatureunder argon. The mixture was stirred for 15 min. Theindole (1a) (131 mg, 1.0 mmol) was added dropwise to this solutionat room temperature. The resulting solution was stirredfor 3 h, and then 0.5 mol/L Na2CO3 was added to quench thereaction. The resulting mixture was extracted with CH2Cl2.The organic layer was washed with saturated brine, dried(MgSO4), and evaporated. The crude product was purifiedusing silica gel chromatography to provide 3aa (226 mg, 82%yield).

References:

Mizoi, Kenta;Mashima, Yu;Kawashima, Yuya;Takahashi, Masato;Mimori, Seisuke;Hosokawa, Masakiyo;Murakami, Yasuoki;Hamana, Hiroshi [Chemical and Pharmaceutical Bulletin,2015,vol. 63,# 7,p. 538 - 545]