Reacción #496388

Ecuación de reacción

1-bromo-8-(4-fluoro-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester

copper(I) cyanide

→

title compound

Rendimiento 45.8%

1-Cyano-8-(4-fluoro-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester

Rendimiento 45.8%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas refluxed for ten minutes before it
2. 2
   Otroquenched with water
3. 3
   Filtraciónfiltered
4. 4
   LavadoThe organic layer was washed with water, brine
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   Otropurified by flash column chromatography on silica gel with a gradient of methanol and dichloromethane

Procedimiento

A mixture of 1-bromo-8-(4-fluoro-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester (400 mg, 1.02 mmol) and copper(I) cyanide (183 mg, 2.04 mmol) in anhydrous dimethylformamide (4 mL) was refluxed for ten minutes before it was cooled to room temperature and quenched with water. The slurry was stirred with chloroform/isopropanol (3:1, 70 mL) and water for ten minutes and filtered. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by flash column chromatography on silica gel with a gradient of methanol and dichloromethane to give the title compound as a white solid (158 mg): MS: (+) m/z 339.07 (M+1).

Fuente