Pyridine → N-(2-(4,4-dimethyl-6-(trifluoromethyl)-1,2,3,4-tetrahydroquinolin-2-yl)phenyl)-2-fluorobenzenesulfonamide

HRID 1036923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1036923
[CH3:1][C:2]1([CH3:23])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[NH:5][CH:4]([C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[NH2:18])[CH2:3]1.N1C=CC=CC=1.[F:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[S:37](Cl)(=[O:39])=[O:38]>ClCCl.O>[CH3:1][C:2]1([CH3:23])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:13])([F:15])[F:14])[CH:10]=2)[NH:5][CH:4]([C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[NH:18][S:37]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[F:30])(=[O:39])=[O:38])[CH2:3]1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 1377612-Fluorobenzenesulphonyl chlorideHCID 672899892-(4,4-Dimethyl-6-(trifluoromethyl)-1,2,3,4-tetrahydroquinolin-2-yl)aniline

Produkt 1

HCID 56967070N-(2-(4,4-dimethyl-6-(trifluoromethyl)-1,2,3,4-tetrahydroquinolin-2-yl)phenyl)-2-fluorobenzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(4,4-dimethyl-6-(trifluoromethyl)-1,2,3,4-tetrahydroquinolin-2-yl)aniline (100 mg, 0.36 mmol) and pyridine (114 mg, 1.44 mmol) in anhydrous dichloromethane (5 mL) was added 2-fluorobenzene-1-sulfonyl chloride (70.1 mg, 0.36 mmol) at ice-bath. After addition, the resulting mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with water, and extracted with dichloromethane. The combined organic layer was dried over anhydrous sodium sulfate, concentrated. The residue was purified by HPLC to give N-(2-(4,4-dimethyl-6-(trifluoromethyl)-1,2,3,4-tetrahydroquinolin-2-yl)phenyl)-2-fluorobenzenesulfonamide. LC/MS m/e obsd. (ESI+) [(M+H)+] 478.90.

Aufarbeitung

  1. additionAfter addition
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-dcf75938c1dd4cd186fe4cf74283cab8
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546427B2

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