4-Chloro-2-fluorobenzene-1-sulfonyl chloride → 4-Chloro-2-fluoro-N-(6-fluoroquinolin-8-yl)-benzenesulfonamide

HRID 513475Notes

Reaction equation

HRID 513475 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.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[C:16]([F:24])[CH:15]=1>CN(C1C=CN=CC=1)C>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH:12][C:10]2[CH:11]=[C:2]([F:1])[CH:3]=[C:4]3[C:9]=2[N:8]=[CH:7][CH:6]=[CH:5]3)(=[O:21])=[O:22])=[C:16]([F:24])[CH:15]=1

Participants

4

Reactant 2

HCID 27788604-Chloro-2-fluorobenzene-1-sulfonyl chlorideHCID 132279926-Fluoroquinolin-8-amine2×

Product 1

HCID 681832594-Chloro-2-fluoro-N-(6-fluoroquinolin-8-yl)-benzenesulfonamideYield 43%

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) (150 mg, 0.93 mmol), 4-chloro-2-fluorobenzenesulfonyl chloride (250 mg, 1.11 mmol) and DMAP (cat.) gave the title compound (140 mg, 43%) after purification by column chromatography with DCM/n-hexane (4:1) as the eluent.

Sources & evidence

ORD record
ord-80d9341615dd4f11882c2998d1f3d18b
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…