Sodium Carbonate → HCID 123662034, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve 1-[(1S,3R)-5-bromo-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl]-2-(2,6-dichlorophenyl)ethanone (300 mg, 0.54 mmol) and vinylboronic acid dibutyl ester (0.24 mL, 1.08 mmol) in 1,4-dioxane (5.4 mL). Add aqueous Na2CO3 solution (2.7 mL, 2M in water). Degas with nitrogen 10 min Add bis(triphenylphosphine)palladium(II) chloride (76 mg, 0.11 mmol). Heat to 80° C. Stir 2 hours. Add water and extract with ethyl acetate three times. Combine the ethyl acetate extracts, dry over sodium sulfate, filter, and concentrate under reduced pressure to give a residue. Purify the residue by silica gel chromatography, eluting with ethyl acetate:hexanes (gradient, 5-80%) to give the title compound as a white foam (220 mg, 0.44 mmol). MS (m/z): 504 (M+1).

Provenance & Evidence