Potassium Carbonate → HCID 86727585, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-7-bromo-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (Preparation #10, Step E, 5.0 g, 16.88 mmol), (2-fluorophenyl)boronic acid (3.54 g, 25.32 mmol), K2CO3 (4.67 g, 33.78 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (2.76 g, 3.37 mmol) in dioxane (60 mL) and water (10 mL) was stirred at 90° C. for 2 h. The reaction mixture was cooled to ambient temperature and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel (eluting with 10-50% EtOAc in petroleum ether) to give (R)-7-(2-fluoro-phenyl)-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (2.5 g, 46%) as a red solid. 1H NMR (400 MHz, DMSO-d6) δ 10.81 (s, 1H), 7.51 (m, 1H), 7.43-7.13 (m, 6H), 4.83 (q, J=6.4 Hz, 1H), 4.69-4.60 (d, J=13.2 Hz, 2H), 1.33 (d, J=6.4 Hz, 3H).

Provenance & Evidence