反应 #1951037

反应方程式

5,6-Dichloro-2-bromo-3-formyl-1-(5-O-acetyl-β-D-ribofuranosyl)indole

sodium methoxide

MeOH H2O

→

4.137

收率 47.0%

5,6-Dichloro-2-bromo-3-formyl-1-(β-D-ribofuranosyl)indole

收率 47.0%

溶剂

MeOH

MeOH

反应条件

后处理

1. 1
   其他was consumed (TLC)
2. 2
   workup.ADDITIONWater (30 mL) was added
3. 3
   其他the solution evaporated until the MeOH
4. 4
   其他was completely removed
5. 5
   萃取The residual aqueous suspension was extracted with EtOAc (3×30 mL)
6. 6
   洗涤the combined organic extracts washed with brine (20 mL)
7. 7
   干燥dried over MgSO4
8. 8
   过滤filtered
9. 9
   其他evaporated
10. 10
    其他to yield a white solid
11. 11
    workup.ADDITIONFractions containing product
12. 12
    其他evaporated
13. 13
    其他to yield a white solid which
14. 14
    其他was recrystallized from MeOH and H2O

实验过程

5,6-Dichloro-2-bromo-3-formyl-1-(5-O-acetyl-β-D-ribofuranosyl)indole (4.136, 101 mg, 0.22 mmol) was dissolved in dry MeOH (10 mL) to which was added sodium methoxide (25 mg, 0.46 mmol). The solution was stirred at room temperature for 15 min, until the starting material was consumed (TLC). Water (30 mL) was added and the solution evaporated until the MeOH was completely removed. The residual aqueous suspension was extracted with EtOAc (3×30 mL) and the combined organic extracts washed with brine (20 mL), dried over MgSO4, filtered and evaporated to yield a white solid. The solid was dissolved in MeOH (1 mL) and subjected to column chromatography (40×350 mm) on C18-reverse phase silica gel with 75% MeOH/H2O. Fractions containing product were pooled and evaporated to yield a white solid which was recrystallized from MeOH and H2O to yield 43 mg (47%) of 4.137 as a pale tan powder: mp 210-211° C.; Rf0.2 (10% MeOH/CHCl3); 1H-NMR (500 MHz, DMSO-d6): δ 9.95 (s, 1H), 8.69 (s, 1H), 8.28 (s, 1H), 6.06 (d, 1H), 5.49-5.43 (m, 2H, D2O exch.), 5.31 (d, 1H, D2O exch.), 4.44 (q, 1H), 4.18 (m, 1H), 4.04 (d, 1H), 3.77-3.71 (m, 2H). 13C-NMR (125 MHz, DMSO-d6): δ 185.53, 134.05, 128.85, 126.58, 126.47, 125.31, 120.56, 116.00, 114.68, 90.27, 86.55, 71.69, 69.62, 60.98. HRMS (EI) m/z calcd. for C14H12BrCl2NO5 422.9276, found 422.9271. Anal calcd for C14H12BrCl2NO5: C, 39.56; H, 2.85; N, 3.30. Found: C, 39.77; H, 3.03; N, 3.32.

来源