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

HRID 1036954Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1036954
[CH3:1][C:2]1([CH3:20])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[NH:5][CH:4]([C:13]2[CH:14]=[C:15]([NH2:19])[CH:16]=[CH:17][CH:18]=2)[CH2:3]1.N1C=CC=CC=1.[F:27][C:28]1[CH:29]=[C:30]([S:34](Cl)(=[O:36])=[O:35])[CH:31]=[CH:32][CH:33]=1>ClCCl>[F:27][C:28]1[CH:29]=[C:30]([S:34]([NH:19][C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([CH:4]3[CH2:3][C:2]([CH3:20])([CH3:1])[C:11]4[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=4)[NH:5]3)[CH:14]=2)(=[O:36])=[O:35])[CH:31]=[CH:32][CH:33]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 672908283-(4,4,6-Trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine

Produkt 1

HCID 569662053-fluoro-N-[3-(4,4,6-trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-benzenesulfonamideAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a stirred mixture of 3-(4,4,6-trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine (135 mg, 0.5 mmol) in dichloromethane (3 mL) was added pyridine (60 mg, 0.75 mmol) in dichloromethane (2 mL) and 3-fluoro-benzenesulfonyl chloride (108 mg, 0.56 mmol) under nitrogen. The resultant mixture was stirred for 4 h. The reaction mixture was diluted with dichloromethane, washed with water (twice), saturated brine, and dried over magnesium sulfate. Magnesium sulfate was removed by filtration, and after evaporation, the residue was purified on chromatography column (silica gel, petroleum ether: Ethyl acetate=12:1) to afford 80 mg of 3-fluoro-N-[3-(4,4,6-trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-benzenesulfonamide as yellow solid (Yield: 38%). MS (ESI+APCI) M+1=425.2.

Aufarbeitung

  1. washwashed with water (twice), saturated brine
  2. dry with materialdried over magnesium sulfate
  3. customMagnesium sulfate was removed by filtration
  4. customafter evaporation
  5. customthe residue was purified on chromatography column (silica gel, petroleum ether: Ethyl acetate=12:1)

Quellen und Nachweise

ORD-Eintrag
ord-597806d5e319410bbf3ab96daf37cb52
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546427B2

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