反应详情

To tert-butyl 6-(3,5-dimethylisoxazol-4-yl)-2-ethoxy-4-((5-fluoropyridin-2-yl)(hydroxy)methyl)-1H-benzo[d]imidazole-1-carboxylate (57 mg, 0.12 mmol) in dichloromethane (6 mL) was added Dess-Martin periodinane (154.1 mg, 0.34 mmol). After 15 minutes, the reaction was quenched with saturated Na2S2O3(aq) (10 mL) and extracted with dichloromethane (3×10 mL). The combined organics were washed with water (30 mL) and brine (30 mL), and dried over Na2SO4. To the crude solution was added N,N-diisopropylethylamine (0.05 mL, 0.26 mmol), 4-(dimethylamino)pyridine (6.8 mg, 0.05 mmol), and di-tert-butyl dicarbonate (120.9 mg). After 90 minutes, the reaction mixture was washed with water (2×30 mL), dried over Na2SO4, and concentrated in vacuo. Purification by flash chromatography (0-50% ethyl acetate/hexane) afforded tert-butyl 6-(3,5-dimethylisoxazol-4-yl)-2-ethoxy-4-(5-fluoropicolinoyl)-1H-benzo[d]imidazole-1-carboxylate as an amber residue.

1. customthe reaction was quenched with saturated Na2S2O3(aq) (10 mL)
2. extractionextracted with dichloromethane (3×10 mL)
3. washThe combined organics were washed with water (30 mL) and brine (30 mL)
4. dry with materialdried over Na2SO4
5. waitAfter 90 minutes
6. washthe reaction mixture was washed with water (2×30 mL)
7. dry with materialdried over Na2SO4
8. concentrationconcentrated in vacuo
9. customPurification by flash chromatography (0-50% ethyl acetate/hexane)