Water → 3-(1-Methyl-4-piperidinyl)-1-[3-(trifluoromethyl)phenyl]-1H-indazole

HRID 1722146

Reaktionsgleichung

Reaktionsgleichung von HRID 1722146
[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:21]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:24][CH:25]=1.O>CN(C)C=O>[CH3:3][N:4]1[CH2:5][CH2:6][CH:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[N:11]=2)[CH2:8][CH2:9]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 67867alpha,alpha,alpha,3-TetrafluorotolueneHCID 178480237HCID 178480237, Verbindung

Produkt 1

HCID 140325833-(1-Methyl-4-piperidinyl)-1-[3-(trifluoromethyl)phenyl]-1H-indazoleAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a stirred suspension of 4.9 g of a 50% oil dispersion of sodium hydride in 60 ml of dimethylformamide was added dropwise a solution a 10.0 g of 3-(1-methyl-4-piperidinyl)-1H-indazole in 80 ml of hot dimethylformamide. The reaction mixture was stirred for 1 hr and then 15.2 g of 3-fluorobenzotrifluoride was added. The reaction was heated at 90° C. for 22 hrs, cooled and poured into water. The aqueous mixture was extracted with ether. The ethereal extracts were dried over anhydrous magnesium sulfate and concentrated to give an oil. The oil was flash chromatographed (silica gel, diethylamine-ethyl acetate (1:9)). Evaporation of the appropriate fractions followed by recrystallization twice from hexane yielded 2.96 g (18%) of product, mp 103°-105° C.

Aufarbeitung

  1. temperaturecooled
  2. extractionThe aqueous mixture was extracted with ether
  3. dry with materialThe ethereal extracts were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto give an oil
  6. customchromatographed (silica gel, diethylamine-ethyl acetate (1:9))
  7. customEvaporation of the appropriate fractions
  8. customfollowed by recrystallization twice from hexane

Quellen und Nachweise

ORD-Eintrag
ord-cceeed4ea0554e94bbcb194613abc6c2
Quelldatensatz
uspto-grants-1989_08
Patentnummer
US04853470

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