Pyridine → N-(5-Fluoro-quinolin-8-yl)-2-nitro-4-trifluoromethyl-benzenesulfonamide

HRID 513519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 513519
[F:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[N+:13]([C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=1[S:26](Cl)(=[O:28])=[O:27])([O-:15])=[O:14].N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][S:26]([C:17]2[CH:18]=[CH:19][C:20]([C:22]([F:24])([F:25])[F:23])=[CH:21][C:16]=2[N+:13]([O-:15])=[O:14])(=[O:27])=[O:28])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 27757802-Nitro-4-(trifluoromethyl)benzene-1-sulfonyl chlorideHCID 445582645-Fluoroquinolin-8-amine2×

Produkt 1

HCID 68183389N-(5-Fluoro-quinolin-8-yl)-2-nitro-4-trifluoromethyl-benzenesulfonamideAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a similar fashion using route 14 general procedure 27, 5-fluoro-quinolin-8-ylamine (Intermediate 50) (280 mg, 1.73 mmol), 2-nitro-4-trifluoromethylbenzenesulfonyl chloride (0.6 g, 2.07 mmol), DMAP (cat), pyridine (0.42 ml, 5.19 mmol) and DCM (5 ml) gave the title compound (420 mg, 59%) after purification by column chromatography with DCM/MeOH (98:2) as the eluent.

Quellen und Nachweise

ORD-Eintrag
ord-45747c34636241a6a311f94a69d0f8bf
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102688B2

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