反应详情

Sodium hydride (0.6 mg, 0.025 mmol) was added into the solution of (E)-N-(2-methoxy-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)pyridin-3-yl)acetamide (10 mg, 0.023 mmol) in dry THF (5 mL). The mixture was stirred at room temperature for 45 min. Iodoethane (15 μL, 0.05 mmol) was added dropwise into the mixture and stirred at room temperature for another 2 h. After evaporated to dryness, the residue was diluted with H2O (10 mL) and extracted (2×20 mL CH2Cl2). The combined extracts were extracted with sat. Na2CO3, washed with brine, dried on MgSO4, and filtered. The residue was purified by silica gel chromatography, eluting with PE/EtOAc (1:1, v/v) to afford pure product as a white powder (8 mg, 75%). 1H-NMR (CDCl3): δ 1.02 (t, 3H, J=7.2 Hz, CH3), 1.74 (s, 3H, CH3), 3.42 (m, 2H, CH2), 3.86 (s, 6H, 2×OCH3), 3.87 (s, 3H, OCH3), 3.99 (s, 3H, OCH3), 4.23 (s, 2H, CH2), 6.10 (s, 2H, Ph-H), 7.07 (d, 1H, J=15.6 Hz, CH), 7.05 (d, 1H, J=2.0 Hz, Py-H), 7.77 (d, 1H, J=15.6 Hz, CH), 8.15 (d, 1H, J=2.0 Hz, Py-H); HR-MS (ESI+) m/z: 465.1762 [M+H]+, C22H28N2O7S, requires 464.1617.

1. stirringstirred at room temperature for another 2 h
2. customAfter evaporated to dryness
3. additionthe residue was diluted with H2O (10 mL)
4. extractionextracted (2×20 mL CH2Cl2)
5. extractionThe combined extracts were extracted with sat. Na2CO3
6. washwashed with brine
7. customdried on MgSO4
8. filtrationfiltered
9. customThe residue was purified by silica gel chromatography
10. washeluting with PE/EtOAc (1:1