Triethylamine → 7-Acetyl-4-(3-(6-methoxy-1-oxoisoindolin-2-yl)-2-methylphenyl)-9H-pyrido[3,4-b]indole-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-bromo-4-(3-(6-methoxy-1-oxoisoindolin-2-yl)-2-methylphenyl)-9H-pyrido[3,4-b]indole-1-carboxamide (0.198 g, 0.366 mmol), tributyl(1-ethoxyvinyl)stannane (0.301 mL, 0.914 mmol), bis(triphenylphosphine)palladium(II) chloride (0.039 g, 0.055 mmol), triethylamine (0.071 mL, 0.512 mmol) in 1,4-Dioxane (12 mL) was heated at 125° C. for 16 hr. Upon cooling to room temperature, the reaction mixture was filtered through CELITE®, and the filtrate was concentrated under vacuum. The residue was diluted with THF (40 mL) and stirred with 1 N HCl solution (10 mL) at 50° C. for 1 hr. The solution was concentrated under vacuum, basified with 1 N NaOH solution, and extracted with ethyl acetate (3×40 mL). The combined extract was dried over anhydrous MgSO4. The desired product (0.112 g, 0.222 mmol, 60.7% yield) was isolated as a pale yellow solid by ISCO (40 g silica gel, solid loading, 50-90% ethyl acetate/hexane).

Provenance & Evidence