8-Aminoquinoline → N-Quinolin-8-yl-3-trifluoromethoxy-benzenesulfonamide

HRID 513448Notes

Reaction equation

HRID 513448 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:16]=[C:17]([S:21](Cl)(=[O:23])=[O:22])[CH:18]=[CH:19][CH:20]=1>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:17]2[CH:18]=[CH:19][CH:20]=[C:15]([O:14][C:13]([F:12])([F:25])[F:26])[CH:16]=2)(=[O:23])=[O:22])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 113598-AminoquinolineHCID 27772183-(Trifluoromethoxy)benzene-1-sulfonyl chloride

Product 1

HCID 31779790N-Quinolin-8-yl-3-trifluoromethoxy-benzenesulfonamideYield 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), 3-trifluoromethoxybenzenesulfonyl chloride (200 mg, 0.69 mmol) and DMAP (cat.) gave the title compound (150 mg, 60%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-53380fbf913b4294a2818302b4b5c24b
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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