4-Iodophenol → 1-ethyl-2-(4-hydroxyphenyl)-6-methoxy-1H-indole-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-ethyl-6-methoxy-1H-indole-3-carbonitrile (2.5 g, 12.5 mmol) in 21 mL of THF is added LDA (23 mL, 22.5 mmol) at −78° C. After warming to 0° C. and stirring for 10 min, the mixture is re-cooled to −78° C. and B(O—iPr)3 (4.35 mL, 18.8 mmol) is added. After the addition, the reaction is allowed to warm to room temperature and stirred for about 1 h. 4-iodophenol (2.89 g, 13.1 mmol), PdCl2(dppf) (510 mg, 0.625 mmol), aqueous K2CO3 (25 mL, 50 mmol) and DMF (42 mL) is added and the reaction mixture is stirred at room temperature overnight. The organic solvent is evaporated under reduced pressure. The residue is washed with water and the mixture is filtered. The filtrate is concentrated to afford crude solid which is purified via column chromatography on silica gel using EtOAc/petroleum ether (1/5 to 2/1) as eluant to yield 73% of 1-ethyl-2-(4-hydroxyphenyl)-6-methoxy-1H-indole-3-carbonitrile.

Provenance & Evidence