Reacción #79590

Ecuación de reacción

bromoacetonitrile

product

[9-benzyl-4-carbamoyl-7-methoxy-1,2,3,4-tetrahydrocarbazol-5-yl]oxyacetic acid sodium salt

dimethylformamide

sodium hydride

→

titled product

9-benzyl-7-methoxy-5-cyanomethyloxy-1,2,3,4-tetrahydrocarbazole-4-carboxamide

Disolventes

tetrahydrofuran

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with water
2. 2
   Lavadowashed with brine
3. 3
   Secadodried over sodium sulfate
4. 4
   Otroevaporated in vacuo
5. 5
   OtroThe residue was chromatographed on silica gel eluting with a gradient of 0 to 4% methanol in methylene chloride

Procedimiento

A solution of 1.47 gram (4.19 mmol) of the product from Example 3, Part A in 146 ml. of dimethylformamide and 31 ml. tetrahydrofuran was treated with 210 mg. of sodium hydride (60% in mineral oil; 5.24 mmol) for 10 minutes and then with 0.39 ml. (0.66 mmol) of bromoacetonitrile for 3.5 hours. The mixture was diluted with ethyl acetate, washed with water, washed with brine, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a gradient of 0 to 4% methanol in methylene chloride to give the titled product, 1.34 gram, 82%.

Fuente