Sodium Carbonate → HCID 68759408, compound

Participants

Reaction Conditions

Reaction Steps

2 M aqueous Na2CO3 solution (0.69 mL) was added to a mixture of 4-bromo-1-methyl-1H-pyridin-2-one (0.14 g) and 3-{cyclopropyl-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]methyl}-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one (pure diastereomer; 0.35 g) in N,N-dimethylformamide (4 mL). The resulting mixture was sparged with argon for 10 min, before [1,1′-bis(diphenylphosphino)-ferrocene]dichloro-palladium(II) dichloromethane complex (57 mg) was added. The mixture was heated to 100° C. and stirred at this temperature for 4 h. After cooling the mixture to ambient temperature, water was added and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were washed with water and brine and dried (MgSO4). The solvent was evaporated and the residue was purified by HPLC on reversed phase (methanol/water/NH4OH) to afford the title compound. Yield: 0.36 g (52% of theory); LC-MS (Method 1): tR=3.31 min; Mass spectrum (ESI+): m/z=487 [M+H]+.

Provenance & Evidence