Pyridine → 5-Chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(5-fluoropyridin-2-yl)benzenesulfonamide

HRID 1619706Notes

Reaction equation

HRID 1619706 reaction equation
[Cl:1][C:2]1[C:3]([F:13])=[CH:4][C:5]([F:12])=[C:6]([S:8](Cl)(=[O:10])=[O:9])[CH:7]=1.[CH3:14][O:15][C:16]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:17]=1[CH2:18][NH:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=1.N1C=CC=CC=1>ClCCl>[Cl:1][C:2]1[C:3]([F:13])=[CH:4][C:5]([F:12])=[C:6]([S:8]([N:19]([CH2:18][C:17]2[CH:27]=[CH:28][C:29]([O:31][CH3:32])=[CH:30][C:16]=2[O:15][CH3:14])[C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=2)(=[O:10])=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27735275-Chloro-2,4-difluorobenzenesulphonyl chlorideHCID 58042270N-(2,4-dimethoxybenzyl)-5-fluoropyridin-2-amine

Product 1

HCID 580422485-Chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(5-fluoropyridin-2-yl)benzenesulfonamideYield 50.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Chloro-2,4-difluorobenzenesulfonyl chloride (200 mg, 0.81 mmol), N-(2,4-dimethoxybenzyl)-5-fluoropyridin-2-amine (Preparation 106, 255 mg, 0.97 mmol) and pyridine (196 μL, 2.43 mmol) in dichloromethane (3 mL) were stirred at room temperature for 36 hours. The mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (5 g Varian bond-elut cartridge, heptane/ethyl acetate 100/0 to 70/30) to afford the title compound (193 mg) as a gum.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customthe residue was purified by silica gel column chromatography (5 g Varian bond-elut cartridge, heptane/ethyl acetate 100/0 to 70/30)

Sources & evidence

ORD record
ord-8fd43e7cf21d4477983c0cc8f74a813d
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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