Sodium Carbonate → HCID 68153598, compound

Participants

Reaction Conditions

Reaction Steps

A degassed solution of (RS)-3-(3-bromo-phenyl)-5-methoxy-3-methyl-3,6-dihydro-2H[1,4]oxazine (intermediate XI-1) (200 mg, 0.7 mmol) in 1,2-dimethoxyethane (3 ml) and 2-(3,5-dichloro-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (288 mg, 1.1 mmol) was treated consecutively with a solution of sodium carbonate (2M, 0.6 ml), triphenylphosphine (38 mg, 0.1 mmol), and palladium(II)acetate (16 mg, 0.1 mmol). The mixture was heated overnight in a sealed tube at 105° C. For the workup, the reaction mixture was evaporated at reduced pressure and the residue directly purified by chromatography on a silica-amine phase using a gradient of heptane/ethylacetate=100/0 to 60/10 as the eluent. The (RS)-3-(3′,5′-dichloro-biphenyl-3-yl)-5-methoxy-3-methyl-3,6-dihydro-2H-[1,4]oxazine was obtained as a colorless oil (160 mg, 65% of theory). MS (ISP): m/z=350.2 [M+H]+.

Provenance & Evidence