4-Fluorobenzenesulfonyl chloride → N-(2-Bromo-pyridin-3-yl)-4-fluoro-benzenesulfonamide

HRID 1716281Notes

Reaction equation

HRID 1716281 reaction equation
[NH2:1][C:2]1[C:3]([Br:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>ClCCl.N1C=CC=CC=1>[Br:8][C:3]1[C:2]([NH:1][S:16]([C:13]2[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=2)(=[O:18])=[O:17])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 6428163-Amino-2-bromopyridine

Product 1

HCID 86619934N-(2-Bromo-pyridin-3-yl)-4-fluoro-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-amino-2-bromo-pyridine (0.4 g, 2.3 mmol) in dichloromethane (4 ml) and pyridine (4 ml) was added 4-fluoro-benzenesulfonylchloride (0.45 g, 2.3 mmol) in one portion. The mixture was stirred overnight. The mixture was diluted with dichloromethane and washed with saturated NaCl solution. The organic layer was dried over sodium sulfate and concentrated. The crude product was purified through chromatography (2-5% EtOAc in dichloromethane). MS 331.8 (M+H)+

Workup

  1. washwashed with saturated NaCl solution
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe crude product was purified through chromatography (2-5% EtOAc in dichloromethane)

Sources & evidence

ORD record
ord-7835a80f5e544a4eaccc53c5708fcdb0
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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