4-Fluorobenzenesulfonyl chloride → HCID 68718101, compound

Participants

Reaction Steps

NaH (6 mg, 0.14 mmol, 60% in mineral oil) was added to tert-butyl 4-[(6-methoxy-1H-indol-4-yl)methyl]piperazine-1-carboxylate (10 mg, 0.029 mmol; Intermediate 40) in dry THF (1 mL). The reaction mixture was stirred for 5 min, 4-fluorobenzenesulfonyl chloride (8 mg, 0.044 mmol) in dry THF (0.5 mL) was added and the mixture was stirred over night. The reaction mixture was cooled on ice and quenched with ice and THF was evaporated. The residue was dissolved in MeOH (3 mL) and conc. HCl (0.5 mL) was added. The mixture was irradiated by microwaves at 100° C. for 300 s, the volume concentrated to ˜1.5 mL, followed of filtering and purification by preparative HPLC/UV (System A, 25-55% MeCN, 0.1% NH4OAc). The title compound (5 mg, 39%) was obtained as a white solid. MS (ESI+) for C20H22FN3O3S m/z 404 (M+H)+.

Provenance & Evidence