Phenol → HCID 11818359, compound

Participants

Reaction Steps

React 3-diazo-3H-indole-2-carboxylic acid ethyl ester, 5, (300 mg, 1.38 mmol) with phenol (5.0 equiv., 650 mg, 6.90 mmol) as described in General Synthetic Procedure VIII. Purify by flash chromatography to afford 3-phenoxy-1H-indole-2-carboxylic acid ethyl ester 6 (R1=phenyl, 303 mg, 78%) as a yellow solid. Hydrolyze the ester to the carboxylic acid 7 (R1=phenyl) 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 Il as a light purple solid, tlc (silica gel) Rf=0.15.

Provenance & Evidence