HCID 178437815, compound → HCID 178437816, compound

HRID 216403Notes

Reaction equation

HRID 216403 reaction equation
[CH3:1][C:2]([CH3:32])([CH3:31])[CH2:3][C:4]1[N:5]=[C:6]([CH2:11][C:12]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][N:25]=3)=[CH:20][CH:19]=2)([OH:17])[C:13]([F:16])([F:15])[F:14])[NH:7][C:8]=1[CH:9]=[CH2:10]>CO.[Pd]>[CH3:31][C:2]([CH3:1])([CH3:32])[CH2:3][C:4]1[N:5]=[C:6]([CH2:11][C:12]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][N:25]=3)=[CH:20][CH:19]=2)([OH:17])[C:13]([F:16])([F:15])[F:14])[NH:7][C:8]=1[CH2:9][CH3:10]

Participants

4

Reactant 1

HCID 178437815HCID 178437815, compound

Product 1

HCID 178437816HCID 178437816, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd (10 wt % on activated carbon) (ca. 1 mg, cat.) was added to a degassed solution of 3-[4-(2,2-dimethylpropyl)-5-vinyl-1H-imidazol-2-yl]-1,1,1-trifluoro-2-[4-(5-fluoropyridin-2-yl)phenyl]propan-2-ol (3 mg, 0.007 mmol) in methanol (1 mL). After stirring under an atmosphere of hydrogen for 1 h, the reaction mixture was filtered through celite rinsing with methanol. The filtrate was concentrated in vacuo to afford the title compound. 1H NMR (500 MHz, CD3OD) δ 8.53 (d, J=3.0 Hz, 1H), 7.99 (d, J=8.4 Hz, 2H), 7.90 (dd, J=4.3, 8.8 Hz, 1H), 7.72-7.60 (m, 4H), 3.63 (bs, 2H), 2.52 (1, J=7.6 Hz, 2H), 2.38 (AB, J=14.9 Hz, 2H), 1.10 (t, J=7.6 Hz, 3H), 0.76 (s, 9H).

Workup

  1. filtrationthe reaction mixture was filtered
  2. washthrough celite rinsing with methanol
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-21c16640be814b3582e8ba9288ce7209
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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