反应详情

Ethylmagnesium bromide (3M/ether, 1.53 mL, 4.60 mmol, 1.5 eq.) was added to a stirred solution of 3-((4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-yloxy)methyl)picolinonitrile (960 mg, 3.07 mmol, 1 eq.) in THF (15.0 mL) at −78° C. After addition, the reaction mixture was allowed to warm to rt and quenched with aqueous citric acid solution. The aqueous layer was extracted with EtOAc (2×30 mL). The combined organic layers were washed with NaHCO3(sat) solution and brine, dried over Na2SO4, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give 1-(3-((4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-yloxy)methyl)pyridin-2-yl)propan-1-one (611 mg, 58%) as a colorless oil. LRMS (M+H+) m/z 345.1.

1. additionAfter addition
2. customquenched with aqueous citric acid solution
3. extractionThe aqueous layer was extracted with EtOAc (2×30 mL)
4. washThe combined organic layers were washed with NaHCO3(sat) solution and brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated
7. custompurified on silica gel using
8. additiona mixture of EtOAc and hexanes as eluent