HCID 67972949, compound → HCID 136378634, compound

HRID 623930Notes

Reaction equation

HRID 623930 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[N:22]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[N:25]=3)=[CH:17][N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>CO.O1CCCC1.[C].[Pd]>[F:29][C:26]([F:27])([F:28])[C:24]1[N:25]=[C:21]([C:18]2[CH:19]=[CH:20][C:15]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)=[N:16][CH:17]=2)[N:22]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:35])[CH3:36])[CH:23]=1

Participants

6

Reactant 2

HCID 67972949HCID 67972949, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 136378634HCID 136378634, compoundYield 95.9%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In methanol (8 mL) and tetrahydrofuran (6 mL) was dissolved 2-[4-(benzyloxy)-phenyl]-5-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]pyridine (0.77 g), and after adding palladium carbon (0.154 g) under nitrogen atmosphere, the atmosphere was replaced by hydrogen, and the mixture was stirred at room temperature for 5 hours. Insoluble material was filtered off by using a membrane filter, and the filtrate was concentrated under reduced pressure. The concentrate was diluted with methanol, activated charcoal was added thereto, and the mixture was filtered by using Celite. The filtrate was concentrated under reduced pressure and crystallized to obtain 4-{5-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)-ethoxy]methyl}-1H-imidazol-2-yl]pyridin-2-yl}phenol (0.612 g).

Workup

  1. filtrationInsoluble material was filtered off
  2. filtrationfilter
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionThe concentrate was diluted with methanol, activated charcoal
  5. additionwas added
  6. filtrationthe mixture was filtered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customcrystallized

Sources & evidence

ORD record
ord-98fd7e9cc2b84a8f8ddfe57c9940f00c
Source dataset
uspto-grants-2016_04
Patent number
US09302996B2

Reaction notes

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