3-(Trifluoromethyl)benzenesulfonyl chloride → N-(2-Bromo-5-chloro-pyridin-3-yl)-3-trifluoromethyl-benzenesulfonamide

HRID 1898028Notes

Reaction equation

HRID 1898028 reaction equation
[Br:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.[F:10][C:11]([F:23])([F:22])[C:12]1[CH:13]=[C:14]([S:18](Cl)(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=1>N1C=CC=CC=1>[Br:1][C:2]1[C:7]([NH:8][S:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([C:11]([F:10])([F:22])[F:23])[CH:13]=2)(=[O:20])=[O:19])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 27696403-Amino-2-bromo-5-chloropyridine

Product 1

HCID 57942301N-(2-Bromo-5-chloro-pyridin-3-yl)-3-trifluoromethyl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 2-bromo-5-chloro-pyridin-3-ylamine (2.07 g, 10.0 mmol) in anhydrous pyridine (20 mL) was added 3-(trifluoromethyl)benzenesulfonyl chloride (4.90 g, 20.0 mmol) and the progress of the reaction was followed by LCMS. The reaction mixture was stirred overnight (18 h), then concentrated to dryness. The residue was dissolved in THF (20 mL) and stirred 18 h with 1M TBAF (20 mL) in THF to cleave the bis-sulfonamide. The THF was subsequently evaporated and the residue was dissolved in ethyl acetate. The organic phase was then washed with water (2×100 mL), brine, and then dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel using ethyl acetate-hexane to provide N-(2-Bromo-5-chloro-pyridin-3-yl)-3-trifluoromethyl-benzenesulfonamide as a white crystalline solid. MS m/z 417.1 (M+H).

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue was dissolved in THF (20 mL)
  3. stirringstirred 18 h with 1M TBAF (20 mL) in THF
  4. customThe THF was subsequently evaporated
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washThe organic phase was then washed with water (2×100 mL), brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-66d685bea4e440039bb6eb3942e4f5d8
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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