Benzenesulfonyl chloride → N-(5-Chloro-6-fluoro-quinolin-8-yl)-benzenesulfonamide

HRID 513481Notes

Reaction equation

HRID 513481 reaction equation
[Cl:1][C:2]1[C:11]([F:12])=[CH:10][C:9]([NH2:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[C:11]([F:12])=[CH:10][C:9]([NH:13][S:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:22])=[O:21])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 681830075-Chloro-6-fluoroquinolin-8-amine2×

Product 1

HCID 68183168N-(5-Chloro-6-fluoro-quinolin-8-yl)-benzenesulfonamideYield 16%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In a similar fashion using route 14 general procedure 27, 5-chloro-6-fluoroquinolin-8-amine (Intermediate 53) (100 mg, 0.51 mmol), benzenesulfonyl chloride (100 mg, 0.61 mmol) and DMAP (cat.) gave the title compound (27 mg, 16%) after purification by column chromatography with DCM as the eluent followed by preparative HPLC (neutral conditions).

Sources & evidence

ORD record
ord-6e5b955f828b41988352d00c875dc99e
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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