Sodium Carbonate → HCID 59380212, compound

Participants

Reaction Conditions

Reaction Steps

A stream of nitrogen was passed through 2-chloro-4-[(3,5-difluorophenyl)sulfonylmethyl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine (0.727 g, 1.8 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.513 g, 2.34 mmol) and 2M aqueous sodium carbonate (3.24 mL, 6.48 mmol) in DMF (3.75 mL), DME (5 mL), ethanol (5 mL) and water (12.5 mL) for 15 minutes. The reaction mixture was treated with dichlorobis(triphenylphosphine)palladium(II) (0.063 g, 0.09 mmol) and the mixture was stirred at 80° C. for 16 hours. The mixture was partitioned between ethyl acetate and water. The organic solution was dried (MgSO4) and concentrated under reduced pressure. The residue was chromatographed on silica, eluting with 25%-60% ethyl acetate in isohexane, to give the desired product as a yellow solid (0.735 g).

Provenance & Evidence