Methanesulfonyl chloride → N-(5-bromo-2-chloro-3-pyridinyl)methanesulfonamide

HRID 445760Notes

Reaction equation

HRID 445760 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]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chloride3×HCID 218583543-Amino-5-bromo-2-chloropyridine

Product 1

HCID 59519513N-(5-bromo-2-chloro-3-pyridinyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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)

Workup

  1. stirringthe RM was stirred for 5 h at rt
  2. stirringthe RM was stirred for 17 h at rt
  3. customThe RM was evaporated to dryness
  4. washwashed with aqueous NaHCO3, with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was absorbed on silica gel
  9. custompurified by flash chromatography (heptane/EtOAc 0% to 40%)
  10. additionThe fractions containing product
  11. customwere evaporated together

Sources & evidence

ORD record
ord-3d697e5d1b75407991a1733d98dd3c9c
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

Loading…