Isopropanol → HCID 68945853, compound

Participants

Reaction Steps

A solution of 1-bromo-3,5-dimethoxybenzene (12.86 g, 59.3 mmol) in THF (60 mL) was cooled to −78° C., evacuated and refilled with nitrogen for 10 cycles. To this clear solution was slowly added n-butyllithium (23.7 mL, 59.3 mmol) and stirred for 30 min. Then a mixture of 1H-Indole-6-carboxylic acid methoxy-methyl-amide (5.50 g, 26.9 mmol) in THF (40 mL) was added and stirred for 3 h at −78° C. The mixture was quenched with isopropanol (12.5 mL, 162 mmol) and added water (40 mL). It was extracted with ether (3×50 mL), washed with water (2×50 mL), dried and concentrated to an oil, which was purified by flash column chromatography (EtOAc/Hexane) to give (3,5-dimethoxy-phenyl)-(1H-indol-6-yl)-methanone as an oil (3.70 g, 49% yield). The product was used in the next step without further purification.

Provenance & Evidence