Sodium Carbonate → HCID 117640808, compound

Participants

Reaction Conditions

Reaction Steps

To N-(6-chloro-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (150 mg, 0.41 mmol), methyl 2-(3-cyano-2-oxo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-1(2H)-yl)acetate (244 mg, 0.61 mmol) and tetrakis(triphenylphosphine)palladium (0) (47 mg, 0.041 mmol) in 1,2-dimethoxyethane (4.5 mL), 2 M Na2CO3 (613.5 μL, 1.23 mmol) was added. The reaction mixture was stirred and heated at 80° C. for 22 hours under N2 atmosphere. The reaction mixture was diluted with ethyl acetate (5 mL), dried over Na2SO4, filtered and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel (0-100% ethyl acetate in hexane) to yield methyl 2-(3-cyano-5-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-methylpyridin-2-yl)-2-oxopyridin-1(2H)-yl)acetate (100 mg, 46.8%). ESI-MS m/z calc. 522.5. found 532.5 (M+1)+. Retention time 1.86 minutes.

Provenance & Evidence