HCID 178418361, compound → HCID 178493422, compound

HRID 620836Notes

Reaction equation

HRID 620836 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:16][C:17]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[C:18]([CH3:20])[N:19]=2)=[C:11]([O:27][CH3:28])[CH:10]=1)C1C=CC=CC=1.[H][H]>CO.O1CCCC1.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:16][C:17]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[C:18]([CH3:20])[N:19]=2)=[C:11]([O:27][CH3:28])[CH:10]=1

Participants

6

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178493376HCID 178493376, compound

Product 1

HCID 178493422HCID 178493422, compoundYield 28%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-benzyloxy-2-methoxyphenyl)-4-methyl-5-(3-pyridyl)imidazole (1.18 g) in methanol (12 ml) and tetrahydrofuran (6 ml) was added 10% palladium on carbon (wet ca. 50%, 0.30 g), and the mixture was stirred for 7 hours at ambient temperature under atmospheric pressure of hydrogen gas. The mixture was filtered, and the filtrate was evaporated. The residue was dissolved in methanol (20 ml), and hydrogenated again on palladium on carbon (wet, 0.50 g) for 5 hours. After the filtration, the filtrate was evaporated, and the residue was triturated in a mixture of diisopropyl ether and isopropanol (1:1 V/V) to give 2-(4-hydroxy-2-methoxyphenyl)-4-methyl-5-(3-pyridyl)imidazole (0.25 g).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in methanol (20 ml)
  4. filtrationAfter the filtration
  5. customthe filtrate was evaporated
  6. customthe residue was triturated in a mixture of diisopropyl ether and isopropanol (1:1 V/V)

Sources & evidence

ORD record
ord-19d19049b97c48ea9a5ea420d814eed2
Source dataset
uspto-grants-1989_04
Patent number
US04822805

Reaction notes

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