Reacción #66222

Ecuación de reacción

6-(benzyl-methyl-amino)-3-(cyano-dimethyl-methyl)-indole-1-carboxylic acid tert-butyl ester

→

[6-(benzyl-methyl-amino)-1H-indol-3-yl]-acetonitrile

Rendimiento 88.2%

Disolventes

DCM TFA

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroEvaporation of solvent
2. 2
   Otrogave a crude, which
3. 3
   Lavadothe solution was washed with water, aqueous sodium bicarbonate and water
4. 4
   Secadodried over MgSO4
5. 5
   OtroEvaporation of solvent
6. 6
   Otrogave a solid, which
7. 7
   Otrowas triturated with hexane

Procedimiento

A solution of 6-(benzyl-methyl-amino)-3-(cyano-dimethyl-methyl)-indole-1-carboxylic acid tert-butyl ester (26.4 g, 90%, 58.9 mmol) in DCM-TFA (2:1, 180 mL) was stirred for 20 h at 20° C. Evaporation of solvent gave a crude, which was redissolved in DCM and the solution was washed with water, aqueous sodium bicarbonate and water and dried over MgSO4. Evaporation of solvent gave a solid, which was triturated with hexane to give [6-(benzyl-methyl-amino)-1H-indol-3-yl]-acetonitrile as a solid (14.3 g). MS (ES): 304 (MH+). [6-(benzyl-methyl-amino)-1H-indol-3-yl]-acetonitrile was then treated in a manner similar to that described in Step 34D-H, but using greater than three equivalents of iodomethane, to give 6-(benzyl(methyl)amino)-1,1-dimethyl-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylic acid ethyl ester.

Fuente