8-Aminoquinoline → N-(quinolin-8-yl)-2-(trifluoromethoxy)benzene-1-sulfonamide

HRID 513446Notes

Reaction equation

HRID 513446 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.[F:12][C:13]([F:26])([F:25])[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21](Cl)(=[O:23])=[O:22]>CN(C1C=CN=CC=1)C>[N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[NH:1][S:21]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][C:13]([F:12])([F:25])[F:26])(=[O:23])=[O:22])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 113598-AminoquinolineHCID 27772152-(Trifluoromethoxy)benzene-1-sulfonyl chloride

Product 1

HCID 17501753N-(quinolin-8-yl)-2-(trifluoromethoxy)benzene-1-sulfonamideYield 60%

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), 2-trifluoromethoxybenzenesulfonyl chloride (200 mg, 0.69 mmol) and DMAP (cat.) gave the title compound (150 mg, 60%) after column purification with DCM elution.

Sources & evidence

ORD record
ord-10a29906df2d445c8b009382405375b2
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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