Sodium hydride → 1-(2-butylsulfanyl-pyrimidin-4-yl)-1H-indole-3-sulfonic acid amide

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Reaction Steps

NaH (147 mg, 3.67 mmol, 60% dispersion) was added to a solution of 1H-indole-3-sulfonic acid amide (600 mg, 3.06 mmol) in DMF (5 mL) at 0° C., and stirred for 15 min. 2-Butylsulfanyl-4-chloro-pyrimidine (682 mg, 3.36 mmol) was added, and washed down with additional DMF (2 mL). The reaction mixture was allowed to warm to RT, and stirred overnight under N2. The reaction mixture was then poured into water, extracted with hot EtOAc, washed with water, brine, and filtered. The mixture was concentrated to half volume, heated on a steam bath, and allowed to crystallize. The resulting white solid was filtered off, washed with DCM, and air-dried to provide 1-(2-butylsulfanyl-pyrimidin-4-yl)-1H-indole-3-sulfonic acid amide (868 mg, 71.4% yield).

Provenance & Evidence