1H-indole-3-sulfonamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). washed down with additional DMF (2 mL) stirred overnight under N2 The reaction mixture was then poured into water extracted with hot EtOAc washed with water, brine filtered The mixture was concentrated to half volume heated on a steam bath to crystallize The resulting white solid was filtered off washed with DCM air-dried

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-Boc 1H-indole-3-sulfonamide (1.47 g, 4.96 mmol) was dissolved in CH3CN (75 mL), and NaI (3.72 g, 24.80 mmol) added. The mixture was cooled to 0° C. under N2, and tri-methylsilyl chloride (TMS-Cl, 2.69 g, 24.80 mmol) added dropwise, the mixture stirred for 15 min at 0° C., then stirred at RT overnight. The mixture was poured into water, the resulting off-white precipitate filtered, washed with water and hexane, and air dried to provide 1H-indole-3-sulfonic acid amide (947 mg, 97% yield), which was used without further purification. stirred at RT overnight the resulting off-white precipitate filtered washed with water and hexane, and air dried