Methyl chloroacetate → methyl 2-(3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-methylpyridin-2-yl)-5-methyl-2-oxopyridin-1(2H)-yl)acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(2′-hydroxy-3,5′-dimethyl-2,3′-bipyridin-6-yl)cyclopropanecarboxamide (0.029 g, 0.06556 mmol) in DMF (1 mL) was added K2CO3 (0.091 mg, 0.6556 mmol) and methyl chloroacetate (28.82 μL, 0.3278 mmol). The reaction was stirred at 80° C. for 21 hours to yield a mixture of N-alkylated product and O-alkylated product. The reaction was filtered using ethyl acetate and the solvent was evaporated under reduced pressure. The crude products were separated by column chromatography on silica gel (0-100% ethyl acetate in hexane) to yield methyl 2-(3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-methylpyridin-2-yl)-5-methyl-2-oxopyridin-1(2H)-yl)acetate [20 mg, 59.3%; ESI-MS m/z calc. 511.47. found 512.5 (M+1)+, retention time 1.74 minutes] and methyl 2-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3,5′-dimethyl-2,3′-bipyridin-2′-yloxy)acetate [8 mg, 24%; ESI-MS m/z calc. 511.47. found 512.5 (M+1)+, retention time 2.13 minutes].

Provenance & Evidence