Reacción #496467

Ecuación de reacción

1-bromo-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester

copper (I) cyanide

→

title compound

Rendimiento 82.7%

1-Cyano-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester

Rendimiento 82.7%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas refluxed for ten minutes before it
2. 2
   Otroquenched with water and ethyl acetate
3. 3
   FiltraciónThe slurry was filtered
4. 4
   LavadoThe organic layer was washed with water, brine
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   Otrothe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes

Procedimiento

A mixture of 1-bromo-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester (1.02 g, 2.63 mmol), copper (I) cyanide (470 mg, 5.25 mmol) and anhydrous dimethylformamide (8.8 mL) was refluxed for ten minutes before it was cooled to room temperature quenched with water and ethyl acetate. The slurry was filtered. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate, concentrated in vacuo and the residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes to give the title compound as a yellow solid (727 mg): MS: (+) m/z 334.83 (M+1).

Fuente