Dimethyl Sulfoxide → 3-(4-oxobutyl)-1H-indole-5-carbonitrile

Temperature

0 °C

18 g of 3-(4-hydroxybutyl)-1H-indole-5-carbonitrile and 34 ml of triethylamine are dissolved in 300 ml of dichloromethane and cooled to about 0° C. in an ice/methanol bath. A solution of 39 g of sulfur trioxide/pyridine complex and 140 ml of dimethyl sulfoxide is subsequently metered in at 2 to 5° C. The mixture is stirred at 2 to 3° C. for approximately a further 20 min., then the reaction solution is warmed to 22-23° C. (room temperature) over the course of 2 hrs. The reaction mixture is diluted by addition of a further 200 ml of dichloromethane and then extracted with water, 10% citric acid solution and 10% sodium chloride solution. The organic phase is concentrated to an oily residue in vacuo, then chromatographed on silica gel using a mixture of dichloromethane and MTB ether.

1. customis subsequently metered in at 2 to 5° C
2. temperaturethe reaction solution is warmed to 22-23° C. (room temperature) over the course of 2 hrs
3. extractionextracted with water, 10% citric acid solution and 10% sodium chloride solution
4. concentrationThe organic phase is concentrated to an oily residue in vacuo
5. customchromatographed on silica gel using
6. additiona mixture of dichloromethane and MTB ether

ORD record

ord-4cfe6c494bb9479cad46e166efb92343

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07799916B2