반응 #2487462

반응 방정식

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

phosphoryl chloride

→

title compound

수율 42.6%

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

수율 42.6%

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   온도cooling
2. 2
   기타The 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
   기타to separate the organic layer
5. 5
   세척The organic layer was washed with saturated brine
6. 6
   건조dried over anhydrous sodium sulfate
7. 7
   농축concentrated under reduced pressure
8. 8
   기타The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

실험 절차

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).

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