Tetrahydrofuran → N-(3,6-dichloropyridazin-4-yl)-4-fluorobenzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a 50 mL round-bottomed flask was added 3,6-dichloropyridazin-4-amine (148 mg, 902 μmol), sodium bis(trimethylsilyl)amide (365 μl, 1805 μmol) and THF (3 mL) at 0° C. The mixture was stirred at 0° C. for 30 min. 4-fluorobenzene-1-sulfonyl chloride (263 mg, 1354 μmol) was then added. The mixture was stirred at 0° C. for 1 hour. The reaction mixture was diluted with satd NH4Cl (10 mL) and extracted with EtOAc (3×30 mL). The combined organic extracts were washed with satd NaCl (5 mL), dried over Na2SO4, filtered and concentrated in vacuo and the residue was purified by silica gel chromatography (5% MeOH/EtOAc) to give N-(3,6-dichloropyridazin-4-yl)-4-fluorobenzenesulfonamide (252 mg, 86.7% yield). MS (ESI positive ion) m/z: 323 (M+1). 1H NMR (300 MHz, DMSO-d6) δ ppm 6.95 (s, 1H) 7.23-7.35 (m, 2H) 7.74-7.84 (m, 2H)

Provenance & Evidence