Tetrahydrofuran → 4-(9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridin-9-yl)phenol

HRID 572178Notes

Reaction equation

HRID 572178 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19]3=[N:20][CH:21]=[CH:22][CH:23]=[C:18]3[N:17]3[CH:24]=[CH:25][N:26]=[C:16]23)=[CH:11][CH:10]=1)C1C=CC=CC=1.C1COCC1>[Pd].CO>[N:26]1[CH:25]=[CH:24][N:17]2[C:18]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[N:15]([C:12]3[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=3)[C:16]=12

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 867049879-[4-(benzyloxy)phenyl]-9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridine

Product 1

HCID 867049864-(9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridin-9-yl)phenolYield 75.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 9-[4-(benzyloxy)phenyl]-9H-imidazo[1′,2′:1,2]imidazo[4,5-b]pyridine (2.48 g), 10% palladium on carbon (containing water (50%), 2.48 g), THF (50 mL) and methanol (50 ml) was stirred under a hydrogen atmosphere at room temperature for 1 hr. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/THF) and recrystallized from ethanol to give the title compound (1.38 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane/THF)
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-7c378b1a7e1f499b80fb2c29bb97afe7
Source dataset
uspto-grants-2015_05
Patent number
US09029388B2

Reaction notes

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