2,6-Difluorobenzenesulfonyl chloride → 2,6-Difluoro-N-(6-fluoro-quinolin-8-yl)-benzenesulfonamide

HRID 513474Notes

Reaction equation

HRID 513474 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([NH2:12])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:15]=1[S:21](Cl)(=[O:23])=[O:22]>CN(C1C=CN=CC=1)C>[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:15]=1[S:21]([NH:12][C:10]1[CH:11]=[C:2]([F:1])[CH:3]=[C:4]2[C:9]=1[N:8]=[CH:7][CH:6]=[CH:5]2)(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 27342712,6-Difluorobenzenesulfonyl chlorideHCID 132279926-Fluoroquinolin-8-amine2×

Product 1

HCID 681833932,6-Difluoro-N-(6-fluoro-quinolin-8-yl)-benzenesulfonamideYield 55%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In a similar fashion using route 14 general procedure 27, 6-fluoroquinolin-8-amine (Intermediate 48) (140 mg, 0.86 mmol), 2,6-difluorobenzenesulfonyl chloride (220 mg, 1.04 mmol) and DMAP (cat.) gave the title compound (160 mg, 55%) after purification by column chromatography with DCM as the eluent followed by recrystallisation with DCM/n-pentane.

Sources & evidence

ORD record
ord-51575ae4fef84c0d841afb858b663333
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…