Indole → 1-(1H-Indol-3-yl)-2-(2-methoxyphenyl)ethanone

Temperature

0 °C

Indole (11.7 g, 100 mmol) was dissolved in diethylether (100 ml) under nitrogen atmosphere and cooled to 0° C. 3M MeMgBr solution (35 ml, 105 mmol) was added dropwise and allowed to stir at room temperature for 2 hours. The reaction mixture was cooled at 0° C. and a solution of 2-methoxybenzoyl chloride 2 (18.46 g, 100 mmol) in diethyl ether (100 ml) was added dropwise with vigorous stirring. The reaction mixture was then allowed to stir at room temperature for 2 hours. A solution of ammonium chloride (300 ml) was added to the reaction mixture and the resulting mixture was stirred at room temperature overnight. The solid that was formed was collected by filtration, washed with water and hexane then dried in a dessicator over phosphorous pentoxide to give 13 g (49%) of 1-(1H-indol-3-yl)-2-(2-methoxyphenyl)ethanone 3 as a cream solid.

1. temperatureThe reaction mixture was cooled at 0° C.
2. stirringto stir at room temperature for 2 hours
3. stirringthe resulting mixture was stirred at room temperature overnight
4. customThe solid that was formed
5. filtrationwas collected by filtration
6. washwashed with water and hexane
7. dry with materialthen dried in a dessicator over phosphorous pentoxide

ORD record

ord-b5376fe189c74b34a9fb1889a1d962d7

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09441033B2