4-Methoxyphenol → HCID 86613184, compound

Participants

Reaction Steps

React 3-diazo-3H-indole-2-carboxylic acid ethyl ester, 5, (231 mg, 1.10 mmol) with 4-methoxyphenol (1.4 equiv., 186 mg, 1.5 mmol) as described in General Synthetic Procedure VIII to afford 3-(4-methoxyphenoxy-1H-indole-2-carboxylic acid ethyl ester 6 (R1=4-methoxyphenyl, 169 mg, 51%) as an ivory-colored solid. Hydrolyze the ester to the carboxylic acid 7 (R1=4-methoxyphenyl) using General Synthetic Procedure IX and then transform the carboxylic acid to the corresponding primary amide as described in General Synthetic Procedure V to afford the title compound Im as a colorless oil, tlc (silica gel) Rf=0.10.

Provenance & Evidence