4-Chloro-3-(trifluoromethyl)benzenesulfonyl Chloride → N-(2-bromo-5-methyl-pyridin-3-yl)-4-chloro-3-trifluoromehtyl-benzenesulfonamide

HRID 419103Notes

Reaction equation

HRID 419103 reaction equation
[Br:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([CH3:9])=[CH:4][N:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][C:12]=1[C:21]([F:24])([F:23])[F:22]>N1C=CC=CC=1>[Br:1][C:2]1[C:7]([NH:8][S:17]([C:14]2[CH:15]=[CH:16][C:11]([Cl:10])=[C:12]([C:21]([F:24])([F:22])[F:23])[CH:13]=2)(=[O:19])=[O:18])=[CH:6][C:5]([CH3:9])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 27807194-Chloro-3-(trifluoromethyl)benzenesulfonyl ChlorideHCID 123624482-Bromo-5-methylpyridin-3-amine

Product 1

HCID 57942390N-(2-bromo-5-methyl-pyridin-3-yl)-4-chloro-3-trifluoromehtyl-benzenesulfonamideYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-bromo-5-methyl-pyridin-3-ylamine (1 g, 5.38 mmol) and 4-chloro-3-trifluoromethylbenzenesulfonylchloride (1.8 g, 6.46 mmol) in pyridine (5 mL) was stirred at 60° C. for 12 h. The mixture was concentrated under reduced pressure and to it, was added 1:1 EtOAc-10% aqueous HCl (50 mL). Aqueous layer was separated and extracted with EtOAc (2×50 mL). Combined EtOAc layers were washed with 10% aqueous HCl (50 mL), dried (anhydrous Na2SO4), concentrated and column purified (SiO2, 50% EtOAc-hexanes) to obtain N-(2-bromo-5-methyl-pyridin-3-yl)-4-chloro-3-trifluoromethyl-benzenesulfonamide (1.42 g) in 84% yield as a half white solid. ESMS m/z (relative intensity): 429 (M+H)+ (100).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure and to it
  2. additionwas added 1:1 EtOAc-10% aqueous HCl (50 mL)
  3. customAqueous layer was separated
  4. extractionextracted with EtOAc (2×50 mL)
  5. washCombined EtOAc layers were washed with 10% aqueous HCl (50 mL)
  6. dry with materialdried (anhydrous Na2SO4)
  7. concentrationconcentrated
  8. customcolumn purified (SiO2, 50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-2f7c70cf0df94d31806b76f17b37dab5
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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