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

HRID 2109627Notes

Reaction equation

HRID 2109627 reaction equation
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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

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, Step A), 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.

Workup

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

Sources & evidence

ORD record
ord-ec67eeed6dd84083a586200036a31879
Source dataset
uspto-grants-2009_04
Patent number
US07514564B2

Reaction notes

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