反应详情

To a solution of 4-(benzyloxy)pyridin-3-amine (40 g, 0.2 mol) and Et3N (60.6 g, 0.6 mol) in DCM (600 mL), MsCl (45.8 g, 0.4 mol) was added dropwise at 0° C. The mixture was allowed to warm up to room temperature and stirred overnight. The reaction mixture was quenched with NaHCO3 and extracted with DCM. The organic phase was washed with brine, dried over Na2SO4, and concentrated. The residue was dissolved in THF:H2O=5:1 (500 mL) and LiOH.H2O (16.8 g, 0.4 mmol) was added. The mixture was stirred for 4 hours at room temperature. EtOAc (300 mL) was added, and the organic phase washed with NaHCO3 (sat., a.q.), brine, dried over Na2SO4, filtrated and concentrated to give pure N-(4-(benzyloxy)pyridin-3-yl)methanesulfonamide (30.0 g, yield: 54.0%). 1H-NMR (CDCl3, 400 MHz) δ 8.67 (s, 1H), 8.34 (d, J=5.6 Hz, 1H), 7.35˜7.42 (m, 5H), 6.91 (d, J=5.6 Hz, 1H), 6.61 (br, 1H), 5.15 (s, 2H), 2.96 (s, 3H). MS (M+H)+: 279.

1. customThe reaction mixture was quenched with NaHCO3
2. extractionextracted with DCM
3. washThe organic phase was washed with brine
4. dry with materialdried over Na2SO4
5. concentrationconcentrated
6. dissolutionThe residue was dissolved in THF
7. stirringThe mixture was stirred for 4 hours at room temperature
8. washthe organic phase washed with NaHCO3 (sat., a.q.), brine
9. dry with materialdried over Na2SO4
10. filtrationfiltrated
11. concentrationconcentrated