反应详情

Dissolve 6-bromomethyl-pyridine-3-carbonitrile (6.2 g, 31.4 mmol) in anhydrous DMF (60 mL) under nitrogen. Add tert-butylthiol (5.32 mL, 47.2 mmol) followed by cesium carbonate (15.3 g, 47.2 mmol) and stir the resulting suspension overnight. Dissolve the reaction mixture in DCM (200 mL) and add water (200 mL). Extract the aqueous phase with DCM (2×200 mL) and dry the combined organic extracts over MgSO4. Filter, add silica gel and concentrate the mixture in vacuo. Purify the residue by chromatography on silica gel (40 g) eluting with cyclohexane/EtOAc (98:2 to 65:35 gradient) to obtain the desired material as a yellow solid (4.92 g, 76%). MS (ES+) m/z: 207 (M+H)+.

1. extractionExtract the aqueous phase with DCM (2×200 mL)
2. dry with materialdry the combined organic extracts over MgSO4
3. filtrationFilter
4. additionadd silica gel
5. concentrationconcentrate the mixture in vacuo
6. customPurify the residue by chromatography on silica gel (40 g)
7. washeluting with cyclohexane/EtOAc (98:2 to 65:35 gradient)