Potassium Carbonate → HCID 58574162, compound

Participants

Reaction Steps

A solution of 3-bromo-7,7-dimethyl-8,9-dihydro-6H-pyrido[2,1-b]quinazolin-11(7H)-one, 3-bromo-8,8-dimethyl-8,9-dihydro-6H-pyrido[2,1-b]quinazolin-11(7H)-one (2.0 g, 6.4 mmol, 1 equiv), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (2.2 g, 12.8 mmol, 2 eq), K2CO3 (1.76 g, 12.8 mmol, 2 equiv), Pd(OAc)2 (576 mg, 2.56 mmol, 0.4 equiv) and Ph3P (1.34 g, 5.12 mmol, 0.8 equiv) in dioxane (200 mL) was stirred at 85° C. for 4 hours under N2. After that, the reaction mixture was cooled to rt. The reaction was quenched with water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extract was dried over Na2SO4 and concentrated. The crude product was purified by silica gel chromatography to afford 650 mg of 7,7-dimethyl-3-vinyl-8,9-dihydro-6H-pyrido[2,1-b]quinazolin-11(7H)-one and 1.0 g of 8,8-dimethyl-3-vinyl-8,9-dihydro-6H-pyrido[2,1-b]quinazolin-11(7H)-one. MS (ESI): 255 (MH+).

Provenance & Evidence