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

HRID 472099

Reaction equation

HRID 472099 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-7567aa01bda94c738c78c4bf8ce7f168
Source dataset
uspto-grants-2014_01
Patent number
US08633187B2

Linked notes

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