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

HRID 1162490Notes

Reaction equation

HRID 1162490 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 75.3%

Procedure

Following the procedure previously described (Example 44, Step 1), 3-amino-5-bromo-2-chloropyridine (770.0 mg, 3.7 mmol) was reacted with 4-fluorobenzenesulfonyl chloride (0.76 g, 3.9 mmol, Oakwood Products, West Columbia, S.C.) to afford N-(5-bromo-2-chloropyridin-3-yl)-4-fluorobenzenesulfonamide (1.018 g, 75% yield) after recrystallization from CH2Cl2/EtOAc. LCMS (ESI positive ionization) m/z: 366 (M+1); 1 H NMR (400 MHz, DMSO-d6) δ ppm 7.24 (t, J=9.00 Hz, 2H); 7.53 (d, J=2.25 Hz, 1H); 7.58 (d, J=2.25 Hz, 1H); 7.74 (dd, J=8.95, 5.43 Hz, 2H).

Sources & evidence

ORD record
ord-e3b44bc7baae4a429bc3d027267493b2
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

Loading…