Pyridine → 2-Nitro-N-(5-trifluoromethyl-quinolin-8-yl)-benzenesulfonamide

HRID 513524Notes

Reaction equation

HRID 513524 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2.[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25](Cl)(=[O:27])=[O:26])([O-:18])=[O:17].N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25]([NH:13][C:10]1[CH:11]=[CH:12][C:3]([C:2]([F:1])([F:14])[F:15])=[C:4]2[C:9]=1[N:8]=[CH:7][CH:6]=[CH:5]2)(=[O:27])=[O:26])([O-:18])=[O:17]

Participants

6

Reactant 3

HCID 1049PyridineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 103531188-Quinolinamine, 5-(trifluoromethyl)-2×

Product 1

HCID 681832412-Nitro-N-(5-trifluoromethyl-quinolin-8-yl)-benzenesulfonamideYield 57.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 14 general procedure 27, 5-trifluoromethyl-quinolin-8-ylamine (Intermediate 45) (260 mg, 1.2 mmol), 2-nitrobenzene-1-sulfonyl chloride (597 mg, 2.69 mmol), DMAP (cat) and pyridine (0.3 ml, 3.67 mmol) in DCM (5 ml) gave the title compound (275 mg, 56%) after purification by column chromatography with n-hexane/EtOAc (90:10) as the eluent.

Sources & evidence

ORD record
ord-0ea41e43e26040149159197deddd87e8
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…