Reacción #2487462

Ecuación de reacción

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

phosphoryl chloride

→

title compound

Rendimiento 42.6%

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

Rendimiento 42.6%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   OtroThe 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
   Otroto separate the organic layer
5. 5
   LavadoThe organic layer was washed with saturated brine
6. 6
   Secadodried over anhydrous sodium sulfate
7. 7
   Concentraciónconcentrated under reduced pressure
8. 8
   OtroThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Procedimiento

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).

Fuente