3-[4-(benzyloxy)-2-(trifluoromethyl)phenyl]4-methyl-5-(4-phenylbicyclo[2.2.2]oct-1-yl)4H-1,2,4-triazole → 4-[4-methyl-5-(4-phenylbicyclo[2.2.2]oct-1-yl)-4H-1,2,4-triazol-3-yl]-3-(trifluoromethyl)phenol

HRID 22850Notes

Reaction equation

HRID 22850 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([CH3:20])[C:18]([C:21]34[CH2:28][CH2:27][C:24]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)([CH2:25][CH2:26]3)[CH2:23][CH2:22]4)=[N:17][N:16]=2)=[C:11]([C:35]([F:38])([F:37])[F:36])[CH:10]=1)C1C=CC=CC=1>C(OCC)(=O)C.CO.[Pd]>[CH3:20][N:19]1[C:18]([C:21]23[CH2:22][CH2:23][C:24]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)([CH2:25][CH2:26]2)[CH2:27][CH2:28]3)=[N:17][N:16]=[C:15]1[C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][C:11]=1[C:35]([F:37])([F:36])[F:38]

Participants

4

Reactant 1

HCID 225916813-[4-(benzyloxy)-2-(trifluoromethyl)phenyl]4-methyl-5-(4-phenylbicyclo[2.2.2]oct-1-yl)4H-1,2,4-triazole

Product 1

HCID 1357330234-[4-methyl-5-(4-phenylbicyclo[2.2.2]oct-1-yl)-4H-1,2,4-triazol-3-yl]-3-(trifluoromethyl)phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

The 3-[4-(Benzyloxy)-2-(trifluoromethyl)phenyl]-4-methyl-5-(4-phenylbicyclo[2.2.2]oct-1-yl)-4H-1,2,4-triazole (8-E) (27 mg, 0.05 mmol) was dissolved in ethyl acetate/methanol (1:1, 4 mL) to which 10% palladium-on-carbon (4 mg) was added. The reaction was then placed under hydrogen atmosphere and stirred for 3 h at room temperature and pressure. After appropriate evacuation of the hydrogen atmosphere, the palladium was filtered through a filter aid with methanol (40 mL). The filtrate was collected and the solvent removed in vacuo to afford 4-[4-methyl-5-(4-phenylbicyclo[2.2.2]oct-1-yl)-4H-1,2,4-triazol-3-yl]-3-(trifluoromethyl)phenol (8-F). MS: m/z 428 (M+1); 1H NMR (500 MHz, CDCl3): δ 1.92 (6H, m), 2.11 (6H, m), 3.41 (3H, s), 7.17 (2H, m), 7.24 (1H, m), 7.31 (2H, m), 7.38 (3H, m) ppm.

Workup

  1. additionwas added
  2. filtrationAfter appropriate evacuation of the hydrogen atmosphere, the palladium was filtered through a filter aid with methanol (40 mL)
  3. customThe filtrate was collected
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-c4e4213524b64bf1a0bb27c15664fd6a
Source dataset
uspto-grants-2005_02
Patent number
US06849636B2

Reaction notes

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