Sodium Carbonate → HCID 66668618, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-3-(4-bromophenyl)-1-(2-methylpyridin-4-yl)-3-o-tolylpropan-1-one (example 142, step 2; 300 mg, 761 μmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (353 mg, 1.14 mmol), [1,1′-bis(diphenyl-phosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (27.8 mg, 38.0 μmol) in 1,4-dioxane (7.5 mL), water (5 mL) and 2 M aq. sodium carbonate solution (1.14 mL, 2.28 mmol) was heated at 85° C. for 4 h, then after cooling partitioned between sat. aq. ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated. Chromatography (SiO2; heptane-ethyl acetate gradient) produced the title compound (365 mg, 97%). White foam, MS (ESI+): m/z=497.4 ([M+H]+).

Provenance & Evidence