Pyridine → 2-Nitro-N-quinolin-8-yl-4-trifluoromethoxy-benzenesulfonamide

HRID 513542Notes

Reaction equation

HRID 513542 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]([F:14])([F:13])[F:12])[CH:7]=[CH:6][C:5]=1[S:15](Cl)(=[O:17])=[O:16])([O-:3])=[O:2].[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[N+:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]([F:14])([F:13])[F:12])[CH:7]=[CH:6][C:5]=1[S:15]([NH:1][C:4]1[CH:5]=[CH:6][CH:7]=[C:23]2[C:24]=1[N:19]=[CH:20][CH:21]=[CH:22]2)(=[O:17])=[O:16])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 1049PyridineHCID 866697542-Nitro-4-trifluoromethoxy-benzenesulfonyl chloride2×

Product 1

HCID 681832432-Nitro-N-quinolin-8-yl-4-trifluoromethoxy-benzenesulfonamideYield 35%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 14 general procedure 27, 8-aminoqunoline (500 mg, 3.47 mmol), 2-nitro-4-trifluoromethoxy-benzenesulfonyl chloride (Intermediate 221) (1.4 g, 4.51 mmol), pyridine (5 ml), DMAP (cat.) and DCM (3 ml) gave the title compound (500 mg, 35%) after purification by column chromatography with n-hexane/EtOAc (90:10) as the eluent.

Sources & evidence

ORD record
ord-d5b22ca0eeef4f01bf65499d9acfda36
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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