2,4-Difluorobenzenesulfonyl Chloride → N-(5-bromo-2-methoxypyridin-3-yl)-2,4-difluorobenzenesulfonamide

HRID 1096804Notes

Reaction equation

HRID 1096804 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[F:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[S:19](Cl)(=[O:21])=[O:20]>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][S:19]([C:13]2[CH:14]=[CH:15][C:16]([F:18])=[CH:17][C:12]=2[F:11])(=[O:21])=[O:20])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 27342732,4-Difluorobenzenesulfonyl ChlorideHCID 447548695-Bromo-2-methoxypyridin-3-amine

Product 1

HCID 59859951N-(5-bromo-2-methoxypyridin-3-yl)-2,4-difluorobenzenesulfonamideYield 31.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a cooled (0° C.) solution of 5-bromo-2-(methyloxy)-3-pyridinamine (20.3 g, 100 mmol) in pyridine (200 mL) was added slowly 2,4-difluorobenzenesulfonyl chloride (21.3 g, 100 mmol) over 15 min (reaction became heterogeneous). The ice bath was removed and the reaction was stirred at ambient temperature for 16 h, at which time the reaction was diluted with water (500 mL) and the solids filtered off and washed with copious amounts of water. The precipitate was dried in a vacuum oven at 50° C. to give N-[5-bromo-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide (12 g, 31.6 mmol, 31.7% yield) MS(ES)+ m/e 379.0, 380.9 [M+H]+.

Workup

  1. custom(reaction became heterogeneous)
  2. customThe ice bath was removed
  3. additionwas diluted with water (500 mL)
  4. filtrationthe solids filtered off
  5. washwashed with copious amounts of water
  6. customThe precipitate was dried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-30544752fd3e4e97b5bc294e1b2a63be
Source dataset
uspto-grants-2012_03
Patent number
US08138347B2

Reaction notes

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