Water → 1-[2-(Trifluorometyl)phenyl]-3-(1-methyl-4-piperidinyl)-1H-indazole

HRID 867695

Reaktionsgleichung

Reaktionsgleichung von HRID 867695
[H-].[Na+].[CH3:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][N:11]=2)[CH2:6][CH2:5]1.F[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]([F:29])([F:28])[F:27].O>CN(C)C=O>[F:27][C:26]([F:29])([F:28])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([CH:7]2[CH2:6][CH2:5][N:4]([CH3:3])[CH2:9][CH2:8]2)=[N:11]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 9807Benzene, 1-fluoro-2-(trifluoromethyl)-HCID 24758Sodium hydrideHCID 178480237HCID 178480237, Verbindung

Produkt 1

HCID 140325421-[2-(Trifluorometyl)phenyl]-3-(1-methyl-4-piperidinyl)-1H-indazoleAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a stirred suspension 1.0 g of a 50% oil dispersion of sodium hydride in 20 ml of dimethylformamide was added, dropwise, 3.2 g of 3-(1-methyl-4-piperidinyl)-1H-indazole dissolved in 25 ml of hot dimethylformamide. After stirring for one hr at ambient temperature, 3.75 ml of 2-fluorobenzotrifluoride was added. The reaction mixture was heated to 90° C. and stirred for 17 hrs. The mixture was then poured into water, extracted with ether, dried over anhydrous magnesium sulfate and concentrated. The residue was purified using flash chromatography (silica gel, diethylamine-ethyl acetate, 1:9). The appropriate fractions were evaporated. The residue was recrystallized once from hexane, then combined with a previously prepared sample (1.1 g), and recrystallized from hexane to yield 2.17 g (24%) of product, mp 110°-111° C.

Aufarbeitung

  1. temperatureThe reaction mixture was heated to 90° C.
  2. stirringstirred for 17 hrs
  3. extractionextracted with ether
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified
  7. customThe appropriate fractions were evaporated
  8. customThe residue was recrystallized once from hexane
  9. customrecrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-e8705f9da10d40db9649ea31e7b58199
Quelldatensatz
uspto-grants-1988_10
Patentnummer
US04775761

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