8-Aminoquinoline → 4-chloro-2-fluoro-N-(quinolin-8-yl)benzene-1-sulfonamide

HRID 513452Notes

Reaction equation

HRID 513452 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[C:15]([F:23])[CH:14]=1>CN(C1C=CN=CC=1)C>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[N:10]=[CH:9][CH:8]=[CH:7]3)(=[O:20])=[O:21])=[C:15]([F:23])[CH:14]=1

Participants

4

Reactant 2

HCID 113598-AminoquinolineHCID 27788604-Chloro-2-fluorobenzene-1-sulfonyl chloride

Product 1

HCID 88236964-chloro-2-fluoro-N-(quinolin-8-yl)benzene-1-sulfonamideYield 82%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In the similar fashion using route 14 general procedure 27, 8-aminoquinoline (100 mg, 0.69 mmol), 4-chloro-2-fluorobenzenesulfonyl chloride (200 mg, 0.83 mmol) and DMAP (cat.) gave the title compound (190 mg, 82%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-5b4fb98268aa45a99e79739ed819b0cd
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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