Tributylamine → HCID 69143775, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 6-bromoisoquinoline (1.75 g) in dry dimethylformamide (15 mL), under argon, was treated with ethyl crotonate (1.7 mL) then with palladium (II) acetate (0.14 g), then with tri-(o-tolyl)phosphine (0.3 g) and then with tributylamine (8 mL). The suspension was stirred, under argon, at 140° C. for 3.5 hours, then stood at room temperature for 3 days and then evaporated. The residual dark oil was treated with ethyl acetate (50 mL) and the resulting solution was washed with water (30 mL) then twice with brine (25 mL), then dried over magnesium sulfate and then evaporated. The residue was subjected to flash chromatography on silica eluting initially with cyclohexane and then with a mixture of cyclohexane and ethyl acetate (9:1, v/v) to give the title compound as an amber coloured oil which solidified on cooling. MS (ES)=242 (M+H)+.

Provenance & Evidence