Sodium hydride → 5-benzyloxy-4-methyl-9-(2-[N-methyl-N-(2-phenylethyl)-amino]-2-oxoethyl)-9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester

Participants

Reaction Conditions

Reaction Steps

A solution of 1.096 g of 5-benzyloxy-4-methyl-9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester (2.93 mmol) in 2.9 ml of tetrahydrofuran is added to a suspension of 92.2 mg of sodium hydride (3.03 mmol; 80% in mineral oil) at 0° C. under nitrogen, and it is stirred for 10 minutes at 0° C. Then, 750 mg (2.93 mmol) of N-methyl-N-phenylethyl-2-bromoacetamide is added, and it is then stirred for 18 hours at 24° C. It is filtered off on Celite, the filtrate is concentrated by evaporation in a vacuum, and the crude product that is thus obtained is purified on a silica gel column with hexane/0-100% ethyl acetate. In this way, 1.24 g of 5-benzyloxy-4-methyl-9-(2-[N-methyl-N-(2-phenylethyl)-amino]-2-oxoethyl)-9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester is obtained as an amorphous, yellowish-colored solid with a melting point of 69°-74° C.

Provenance & Evidence