Potassium Carbonate → HCID 86718603, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 8-bromo-3-(tert-butyl)-6-(4-fluorophenyl)-3,4-dihydro-2H-benzo[e][1,3]oxazine (2.0 g, 5.49 mmol), 2-(trifluoromethyl)pyridine-5-boronic acid [purchased from Frontier Scientific] (1.26 g, 6.59 mmol) and potassium carbonate (1.52 g, 10.98 mmol) in dimethoxyethane (15 mL) and water (5 mL) was purged with nitrogen for 20 minutes. Tetrakis(triphenylphosphine)palladium(0) (317.2 mg, 0.275 mmol) was added and the reaction mixture heated at 80° C. in a sealed vial for 17 hours. The cooled reaction mixture was partitioned between ethyl acetate (80 mL) and 1.0 M aqueous sodium hydroxide solution (80 mL), the organic phase separated, washed with water (80 mL) and saturated brine (80 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give an orange syrup. The crude product was purified by chromatography on silica eluting with a solvent gradient of 0 to 8% methanol (containing 1% aqueous ammonium hydroxide) in dichloromethane to give 3-(tert-butyl)-6-(4-fluorophenyl)-8-(6-(trifluoromethyl)pyridin-3-yl)-3,4-dihydro-2H-benzo[e][1,3]oxazine (0.773 g, 37% yield) as a colorless syrup.

Provenance & Evidence