Potassium Carbonate → HCID 86727378, compound

Participants

Reaction Conditions

Reaction Steps

A degassed mixture of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.175 g, 0.214 mmol), 6-(1-benzhydryl-3-methyl-azetidin-3-ylamino)-7-bromo-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.220 g, 0.403 mmol), K2CO3 (0.167 g, 1.208 mmol), and phenylboronic acid (0.123 g, 1.006 mmol) in water (0.5 mL) and dioxane (3 mL) was stirred at 100° C. overnight. The mixture was cooled to ambient temperature, the solution was concentrated in vacuo and the residue was purified by column chromatography on silica gel (eluting with 0 to 50% EtOAc in petroleum ether) to give 6-(1-benzhydryl-3-methyl-azetidin-3-ylamino)-4-methyl-7-phenyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.120 g, 55%). 1H NMR (CDCl3, 400 MHz): δ 8.09 (brs, 1H), 7.31 (m, 7H), 7.19 (m, 6H), 7.12 (m, 2H), 6.73 (s, 1H), 5.85 (s, 1H), 4.54 (q, J=6.8 Hz, 1H), 4.49 (d, J=12.8 Hz, 2H), 4.32 (s, 1H), 3.96 (brs, 1H), 3.22 (m, 2H), 2.93 (m, 2H), 1.52 (s, 3H), 1.37 (d, J=6.8 Hz, 3H).

Provenance & Evidence