反应详情

温度

60 °C

To a mixture of 6-(5-bromopyridin-2-ylmethylthio)-3-tert-butoxycarbonyl-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (146 mg, 0.30 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (12 mg, 0.015 mmol) under dry nitrogen add with stirring a solution of 0.5 M cyclohexylzinc bromide in THF (3.0 mL, 1.5 mmol). Degas, purge with dry nitrogen, and stir overnight at 60° C. Cool to ambient temperature, dilute with EtOAc, wash with water, dry over anhydrous MgSO4 and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (5:1) to give 3-tert-butoxycarbonyl-7-chloro-6-(5-cyclohexyl-pyridin-2-ylmethylthio)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as an oil (46 mg, 32%). MS (APCI+) m/z: 487 (M+H)+. Use a method similar to the General Procedure 14 to give the title compound as a white solid. MS (APCI+) m/z: 387 (M+H)+.

1. additionadd
2. customDegas
3. custompurge with dry nitrogen
4. temperatureCool to ambient temperature
5. additiondilute with EtOAc
6. washwash with water
7. dry with materialdry over anhydrous MgSO4
8. concentrationconcentrate in vacuo
9. customPurify by chromatography on silica gel eluting with hexane/EtOAc (5:1)