HCID 86698189, compound → HCID 136378635, compound

HRID 623945Notes

Reaction equation

HRID 623945 reaction equation
[F:1][C:2]([F:39])=[CH:3][C:4]1[N:5]=[C:6]([C:17]2[CH:18]=[CH:19][C:20]([C:23]3[CH:28]=[CH:27][C:26]([O:29]CC4C=CC(OC)=CC=4)=[CH:25][CH:24]=3)=[N:21][CH:22]=2)[N:7]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[CH:8]=1>C(O)C.O1CCCC1.[C].[Pd]>[F:39][CH:2]([F:1])[CH2:3][C:4]1[N:5]=[C:6]([C:17]2[CH:18]=[CH:19][C:20]([C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)=[N:21][CH:22]=2)[N:7]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:14])[CH3:15])[CH:8]=1

Participants

5

Reactant 1

HCID 86698189HCID 86698189, compound

Product 1

HCID 136378635HCID 136378635, compoundYield 56.6%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In ethanol (50 mL) and tetrahydrofuran (20 mL) was dissolved 5-[4-(2,2-difluoroethenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]-2-{4-[(4-methoxybenzyl)oxy]phenyl}pyridine (0.84 g), 10% palladium-carbon (50% water contained, 395 mg) was added to the solution, and the mixture was stirred under hydrogen atmosphere for 24 hours. The reaction mixture was filtered by using a membrane filter, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 4-{5-[4-(2,2-difluoroethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]pyridin-2-yl}phenol (373 mg).

Workup

  1. additionwas added to the solution
  2. filtrationThe reaction mixture was filtered
  3. filtrationfilter
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f7280f1100bf42478c9e566b308b091c
Source dataset
uspto-grants-2016_04
Patent number
US09302996B2

Reaction notes

Loading…