Potassium Carbonate → 1-(2,3-Dihydropyrano[4,3,2-de]quinolin-7-yl)-3-methylnaphthalen-2-ol

Participants

Reaction Conditions

Reaction Steps

1-Bromo-3-methylnaphthalen-2-ol (5B) (340 mg, 1.43 mmol), 2,3-dihydropyrano[4,3,2-de]quinolin-7-ylboronic acid TFA salt (5C) (566 mg, 1.72 mmol), Pd(PPh3)4 (166 mg, 0.14 mmol) and K2CO3 (991 mg, 7.15 mmol) were added to a degassed solution of DMA (6 mL) and water (2 mL) and heated to 110° C. in a microwave for 1 h. The reaction mixture was cooled, diluted with ethyl acetate and washed with saturated sodium bicarbonate solution, brine and dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to give 5D (136 mg, 29%). LCMS-ESf+ (m/z): [M+H]+ calcd for C22H18NO2: 328.38. Found: 328.2.

Provenance & Evidence