Water → HCID 59743501, compound

Participants

Reaction Steps

4-Benzylsulfanyl-1H-indole (5.00 g, 21 mmol) (Can. J. Chem. 1962, 40, 511) was slowly added to a suspension of NaH (60% dispersion in mineral oil, 1.37 g, 34 mmol) in DMF (40 mL) at 0° C. The reaction mixture was stirred for 15 min until the gas evolution ceased, then 2,4-di-chloropyrimidine (3.03 g, 20 mmol) was added portionwise, followed by an additional aliquot of DMF (10 mL). The resulting mixture was slowly warmed to RT, then poured onto a slurry of ice and water and extracted with EtOAc. The organic layer was washed twice with a mixture of water and brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (EtOAc/hexanes, gradient from 10:90 to 50:50) to give 4-benzylsulfanyl-1-(4-chloropyrimidin-2-yl)-1H-indole (979 mg, 14% yield) as a pale-yellow waxy solid and a mixture of 4-benzylsulfanyl-1-(2-chloropyrimidin-4-yl)-1H-indole and the bisubstituted product (691 mg) after precipitation from DCM/EtOAc. This mixture was repurified by flash chromatography (EtOAc/hexanes, 20:80) to give 4-benzylsulfanyl-1-(2-chloropyrimidin-4-yl)-1H-indole (270 mg, 4% yield) as an off-white solid. MS=352 [M+H]+; MP=159.0-161.2° C.

Provenance & Evidence