N,N'-Dimethylethylenediamine → 1-(4-Methylbenzene-1-sulfonyl)-1H-indole-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

An oven dried screw cap test tube was charged with NaCN (106 mg, 2.163 mmol), dried KI (60 mg, 0.361 mmol, 20 mol %), CuI (34 mg, 0.178 mmol, 10 mol %), 5-bromo-1-(toluene-4-sulfonyl)-1H-indole (630 mg, 1.803 mmol), evacuated and backfilled with argon three times. N,N′-dimethylethylenediamine (195 μL, 1.832 mmol) and anhydrous toluene (1.1 mL) were added under argon. The tube was sealed and the reaction mixture was stirred magnetically at 110° C. for 24 h. The resulting yellow suspension was cooled to room temperature, 2 mL of ethyl acetate, 1 mL of ammonium hydroxide (30%) and 1 mL of water were added. The mixture was stirred at 25° C. for 10 min, then the organic layer was separated and the aqueous layer was extracted three times with ethyl acetate (3×2 mL). The organic layers combined were washed with 5 mL of water and dried over MgSO4. The solvent was removed at reduced pressure. Purification of the residue by flash chromatography on silica gel (2×15 cm; hexane/ethyl acetate 10:1) provided 459 mg (86% yield) of the title compound as a white solid.

Provenance & Evidence