Pyridine → N-[2-(4,4-dimethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-3-fluoro-benzenesulfonamide

HRID 1036922Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1036922
[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:32]=[C:33]([S:37](Cl)(=[O:39])=[O:38])[CH:34]=[CH:35][CH:36]=1>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:33]2[CH:34]=[CH:35][CH:36]=[C:31]([F:30])[CH:32]=2)(=[O:39])=[O:38])[CH2:3]1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 672899892-(4,4-Dimethyl-6-(trifluoromethyl)-1,2,3,4-tetrahydroquinolin-2-yl)aniline

Produkt 1

HCID 56967069N-[2-(4,4-dimethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-3-fluoro-benzenesulfonamide

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 (150 mg, 0.47 mmol) and pyridine (148 mg, 1.44 mmol) in anhydrous dichloromethane (5 mL) was added a solution of 3-fluorobenzene-1-sulfonyl chloride (92 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-tetrahydro-quinolin-2-yl)-phenyl]-3-fluoro-benzenesulfonamide 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-5f3195d18a52499f97cdafb7f816d974
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546427B2

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