4-Fluorobenzenesulfonyl chloride → N-(5-bromo-2-chloropyridin-3-yl)-4-fluorobenzenesulfonamide

HRID 252719Notes

Reaction equation

HRID 252719 reaction equation
[NH2:1][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>>[Br:8][C:6]1[CH:7]=[C:2]([NH:1][S:17]([C:14]2[CH:15]=[CH:16][C:11]([F:10])=[CH:12][CH:13]=2)(=[O:19])=[O:18])[C:3]([Cl:9])=[N:4][CH:5]=1

Participants

3

Reactant 2

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 218583543-Amino-5-bromo-2-chloropyridine

Product 1

HCID 53363354N-(5-bromo-2-chloropyridin-3-yl)-4-fluorobenzenesulfonamideYield 82%

Procedure

Using an analogous method to that described in Example 11, 3-amino-5-bromo-2-chloropyridine was reacted with and 4-fluorobenzenesulfonyl chloride to give N-(5-bromo-2-chloropyridin-3-yl)-4-fluorobenzenesulfonamide in 82% yield; 1H NMR Spectrum: (CDCl3) 8.21 (1H, d); 8.15 (1H, d); 7.84 (2H, m); 7.20 (2H, m); 6.97 (1H, br s); Mass Spectrum: M+H+ 365.

Sources & evidence

ORD record
ord-f2a4cd7fb9004fb98099d865f5ea9dbe
Source dataset
uspto-grants-2011_01
Patent number
US07868188B2

Reaction notes

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