Methanesulfonyl chloride → N-(5-bromo-2-chloro-3-pyridinyl)methanesulfonamide
Reaction equation
[NH2:1][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[CH3:10][S:11](Cl)(=[O:13])=[O:12]>N1C=CC=CC=1>[Br:8][C:6]1[CH:7]=[C:2]([NH:1][S:11]([CH3:10])(=[O:13])=[O:12])[C:3]([Cl:9])=[N:4][CH:5]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-amino-5-bromo-2-chloropyridine (stage 152.1.2, 3.59 mmol) in pyridine (7 ml) was added methanesulfonyl chloride (Fluka, Buchs, Switzerland, 0.365 ml). The RM was stirred for 22 h at rt then was added methanesulfonyl chloride (0.2 ml), the RM was stirred for 5 h at rt. Methanesulfonyl chloride (0.2 ml) was added and the RM was stirred for 17 h at rt. The RM was evaporated to dryness and then taken in EtOAc, washed with aqueous NaHCO3, with brine, dried over Na2SO4, filtered and evaporated. The residue was absorbed on silica gel and purified by flash chromatography (heptane/EtOAc 0% to 40%). The fractions containing product were evaporated together to give the title compound as a pink solid. (HPLC: tR 2.91 min (Method A); M+H=285, 287 MS-ES)