Isopropanol → HCID 68943292, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 4-bromo-2-ethoxy-1-methoxy-benzene (6.52 g, 23.7 mmol) and anhydrous THF (20 mL) was cooled to −78° C., evacuated and refilled with nitrogen for 10 cycles. To this clear solution was slowly added n-butyllithium (9.5 mL, 23.7 mmol) and stirred for 20 min. Then a mixture of 1H-indole-6-carboxylic acid methoxy-methyl-amide (2.20 g, 10.8 mmol) in anhydrous THF (25 mL) was added and stirred for 1 hour at −78° C. The mixture was quenched with isopropanol (4.9 mL, 65 mmol) and water (15 mL). The mixture was extracted with EtOAc (3×50 mL). The combined organic phases were washed with water (2×50 mL), dried over MgSO4 and concentrated to give an oil, which was purified by flash column chromatography (EtOAc, Hexane) to give (3-ethoxy-4-methoxy-phenyl)-(1H-indol-6-yl)-methanone as an oil (2.30 g). The product was used in the next step without further purification.

Provenance & Evidence