Potassium Carbonate → 3-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-(trifluoromethyl)benzenamine

HRID 887581Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 887581
CC1(C)C(C)(C)OB([C:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH:10]=2)O1.C([O-])([O-])=O.[K+].[K+].[NH2:23][C:24]1[CH:25]=[C:26]([C:31]([F:34])([F:33])[F:32])[CH:27]=[C:28](Br)[CH:29]=1>CN(C=O)C.CCOC(C)=O>[CH3:15][N:12]1[CH2:13][CH2:14][C:9]([C:28]2[CH:27]=[C:26]([C:31]([F:32])([F:34])[F:33])[CH:25]=[C:24]([NH2:23])[CH:29]=2)=[CH:10][CH2:11]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 27358803-Bromo-5-(trifluoromethyl)anilineHCID 207733711-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine

Produkt 1

HCID 219596433-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-(trifluoromethyl)benzenamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of 4,4,5,5-tetramethyl-2-(1-methyl(4-1,2,5,6-tetrahydropyridyl))-1,3,2-dioxaborolane (1.0 g, 4.4 mmol), PdCl2pddf (0.16 g, 0.2 mmol) and K2CO3 (1.8 g, 13.2 mmol) and 3-amino-5-bromobenzotrifluoride (0.8 g, 3.3 mmol) in DMF (25 mL) was heated at 80° C. for 16 h. The resulting mixture was diluted with EtOAc, washed with H2O, dried over Na2SO4, and concentrated. The residue was purified by SiO2 chromatography to give the title intermediate. MS (ES+): 257 (M+H)+. Calc'd C13H15F3N2—256.3.

Aufarbeitung

  1. washwashed with H2O
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by SiO2 chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cb91188eeab14b3ebfb596fb4646a33a
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247430B2

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