反应 #2487462

反应方程式

6-[6-fluoro-5-methoxy-2-(thiophen-3-yl)indol-1-ylmethyl]pyridine-2-carboxamide

phosphoryl chloride

→

title compound

收率 42.6%

6-[6-Fluoro-5-methoxy-2-(thiophen-3-yl)indol-1-ylmethyl]pyridine-2-carbonitrile

收率 42.6%

溶剂

N,N-dimethylformamide

反应条件

后处理

1. 1
   温度cooling
2. 2
   其他The reaction mixture was quenched with a saturated aqueous sodium hydrogen carbonate solution (10 mL)
3. 3
   workup.ADDITIONEthyl acetate and water were then added to the mixture
4. 4
   其他to separate the organic layer
5. 5
   洗涤The organic layer was washed with saturated brine
6. 6
   干燥dried over anhydrous sodium sulfate
7. 7
   浓缩concentrated under reduced pressure
8. 8
   其他The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

实验过程

To a solution of 6-[6-fluoro-5-methoxy-2-(thiophen-3-yl)indol-1-ylmethyl]pyridine-2-carboxamide (165 mg) in N,N-dimethylformamide (2.1 mL) was added phosphoryl chloride (0.058 mL) under ice-cooling. This mixture was stirred for 50 minutes. The reaction mixture was quenched with a saturated aqueous sodium hydrogen carbonate solution (10 mL). Ethyl acetate and water were then added to the mixture to separate the organic layer. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (67 mg). 1H-NMR (CDCl3) δ ppm: 3.94 (3H, s), 5.47 (2H, s), 6.62 (1H, s), 6.80 (1H, d, J=8.3 Hz), 6.87 (1H, d, J=11.3 Hz), 7.10-7.30 (3H, m), 7.35-7.45 (1H, m), 7.59 (1H, d, J=7.7 Hz), 7.65-7.75 (1H, m).

来源