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

HRID 1438464Notes

Reaction equation

HRID 1438464 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 1 M 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 1 M 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-b1571531d6c84755a15c8335a423e2be
Source dataset
uspto-grants-2009_11
Patent number
US07622583B2

Reaction notes

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