2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1-methyl-N-(3,4,5-trimethoxyphenyl)-1H-indole-5-sulfonamide

Participants

Reaction Conditions

Reaction Steps

A 0° C. slurry of N-(3,4,5-trimethoxyphenyl)-1-methylindoline-5-sulfonamide (11.3 g, 0.030 mol) in THF (130 mL) was treated with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (7.15 g, 0.0315 mol), stirred for 4 hours, warmed to 25° C., and stirred for 10 hours. The mixture was concentrated to half of its original volume, diluted with methyl tert-butyl ether (70 mL), cooled to 0° C., stirred for 2 hours, and filtered. The resulting solid was washed with methyl tert-butyl ether (50 mL), dried, and recrystallized from acetonitrile and methyl tert-butyl ether to provide 9.2 g of the desired product (81%).

Provenance & Evidence