Potassium Carbonate → HCID 86718574, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6,8-dibromo-3-(tert-butyl)-3,4-dihydro-2H-benzo[e][1,3]oxazine (Intermediate 6) (0.621 g, 1.79 mmol), pyridine-3-boronic acid [purchased from Boron Molecular Limited] (0.660 g, 5.37 mmol) and potassium carbonate (1.979 g, 14.3 mmol) in 2-propanol (30 mL) and water (6 mL) was purged with nitrogen for 20 minutes. Tetrakis(triphenylphosphine)Pd (0) (107 mg, 0.09 mmol) was added and the resulting mixture was heated at 72° C. for 30 minutes then the cooled reaction mixture concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with water, dried (MgSO4), filtered and concentrated under reduced pressure to afford a dark brown oil. The product was purified by flash chromatography on silica eluting with a solvent gradient of 0 to 30% ethyl acetate in hexanes to give 2-((tert-butylamino)methyl)-4,6-di(pyridine-3-yl)phenol (151 mg) as an off-white solid.

Provenance & Evidence