反应详情

温度

5 °C

To a solution of 1-benzenesulfonyl-5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine (165, 1.00 g, 2.16 mmol) in 7 mL of tetrahydrofuran at −50° C. under nitrogen, isopropylmagnesium chloride (1.18 mL, 2.35 mmol) was added slowly. The reaction was warmed to 5° C. over 70 minutes, then cooled to −45° C. and (6-fluoro-5-formyl-pyridin-2-yl)-(4-methoxy-benzyl)-carbamic acid tert-butyl ester (83, 0.678 g, 1.88 mmol) in 3.0 mL of tetrahydrofuran was added. The reaction was allowed to warm to room temperature over 2-3 hours. The reaction was mixed with aqueous 1 N citric acid and extracted with ethyl acetate. The organic layer was washed with water and brine, then dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with ethyl acetate and hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound as a white solid (166, 1.155 g). MS (ESI) [M+H]+=696.4 and 698.3.

1. temperaturecooled to −45° C.
2. temperatureto warm to room temperature over 2-3 hours
3. extractionextracted with ethyl acetate
4. washThe organic layer was washed with water and brine
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. concentrationthe filtrate concentrated under vacuum
8. customThe resulting material was purified by silica gel column chromatography
9. washeluting with ethyl acetate and hexane
10. concentrationconcentrated under vacuum