反应详情

温度

50 °C

To a mixture of 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(2′-methoxy-3,5′-dimethyl-2,3′-bipyridin-6-yl)cyclopropanecarboxamide (0.181 g, 0.05 mmol) in CH3CN (0.5 mL) was added TMSI (114, 0.80 mmol) drop wise at 0° C. The reaction was stirred at 50° C. for 3 hours. The reaction was partitioned between ethyl acetate and H2O and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over MgSO4. After the removal of solvent, the residue was purified by column chromatography (0-10% MeOH-EtOAc) to yield a yellow solid. The solid was re-dissolved in DCM-EtOAc, washed with NaHSO3 (2×), brine, dried over MgSO4 and evaporated to dryness to yield 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(2′-hydroxy-3,5′-dimethyl-2,3′-bipyridin-6-yl)cyclopropanecarboxamide as a white solid (0.148 g, 84%). ESI-MS m/z calc. 439.41. found 440.2 (M+1)+. Retention time 1.51 minutes.

1. customThe reaction was partitioned between ethyl acetate and H2O
2. extractionthe aqueous layer was extracted with ethyl acetate
3. washThe combined organic layers were washed with brine
4. dry with materialdried over MgSO4
5. customAfter the removal of solvent
6. customthe residue was purified by column chromatography (0-10% MeOH-EtOAc)
7. customto yield a yellow solid
8. washwashed with NaHSO3 (2×), brine
9. dry with materialdried over MgSO4
10. customevaporated to dryness