Ethyl Acetate → 1-[7-(6-Chloro-indole-1-sulfonyl)-4,4-dimethyl-3,4-dihydro-1H-isoquinolin-2-yl]-ethanone

Participants

Reaction Steps

Potassium tert-butoxide (37 mg, 0.33 mmol) was added to a stirred solution of 6-chloroindole (50 mg, 0.33 mmol) in dry tetrahydrofuran (1 ml) under argon at room temperature. After stirring for 5 minutes, a solution of 2-acetyl-4,4-dimethyl-1,2,3,4-tetrahydro-isoquinoline-7-sulfonyl chloride (D3) (100 mg, 0.33 mmol) in dry tetrahydrofuran (1 ml) was added and the solution was stirred for a further 3 h. Ethyl acetate (5 ml) and water (5 ml) were added to the reaction mixture, which was then shaken. The layers were separated and the organic phase was washed with brine (5 ml), dried (MgSO4) and concentrated in vacuo to an oil. The oil was purified by column chromatography over silica gel eluting with a gradient of acetone/toluene to afford the title compound (D4) (70 mg, 51%), MS: m/z (MH+) 417/419.

Provenance & Evidence