Benzenesulfonyl chloride → N-(6-Fluoro-quinolin-8-yl)benzenesulfonamide

HRID 513473Notes

Reaction equation

HRID 513473 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.[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C1C=CN=CC=1)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([NH:12][S:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)(=[O:21])=[O:20])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 132279926-Fluoroquinolin-8-amine2×

Product 1

HCID 68183044N-(6-Fluoro-quinolin-8-yl)benzenesulfonamideYield 36%

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) (60 mg, 0.37 mmol), benzenesulfonyl chloride (78 mg, 0.44 mmol) and DMAP (cat.) gave the title compound (40 mg, 36%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-875cb699a6ce4dd5821a4cbb578ac113
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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