Pyridine → 4-Bromo-2-fluoro-N-thiazol-2-yl-benzenesulfonamide

반응식

[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.N1C=CC=CC=1.C(Cl)Cl.[Br:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[C:19]([F:27])[CH:18]=1>>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:1][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)(=[O:24])=[O:25])=[C:19]([F:27])[CH:18]=1

참가 물질

반응물 4

HCID 1049Pyridine

HCID 21552-Aminothiazole

HCID 6344Dichloromethane

HCID 27363104-Bromo-2-fluorobenzene-1-sulfonyl chloride

생성물 1

HCID 251383534-Bromo-2-fluoro-N-thiazol-2-yl-benzenesulfonamide수율 36%

실험 절차

To a solution of 2-aminothiazole (4.51 g, 0.0450 mol) and pyridine (24.26 mL, 0.3000 mol) in methylene chloride (40 mL, 0.6 mol) at 0° C. was added portionwise 4-bromo-2-fluorobenzenesulfonyl chloride (8.2 g, 0.030 mol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, diluted with EtOAc, washed with 1N HCl solution, H2O and brine. The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated to give the crude product that was purified via automated flash chromatography (silica gel, 25% EtOAc in hexanes to 100% EtOAc) to give the product as a light brown solid (3.6 g, 36%).