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

HRID 572190Notes

Reaction equation

HRID 572190 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][C:23]([CH3:24])=[C:18]3[N:17]3[CH:25]=[CH:26][N:27]=[C:16]23)=[CH:11][CH:10]=1)C1C=CC=CC=1.C1COCC1>[Pd].CO>[CH3:24][C:23]1[CH:22]=[CH:21][N:20]=[C:19]2[N:15]([C:12]3[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=3)[C:16]3[N:17]([CH:25]=[CH:26][N:27]=3)[C:18]=12

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 867049939-[4-(Benzyloxy)phenyl]-5-methyl-9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridine

Product 1

HCID 867049944-(5-Methyl-9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridin-9-yl)phenolYield 94.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 9-[4-(benzyloxy)phenyl]-5-methyl-9H-imidazo[1′,2′:1,2]imidazo[4,5-b]pyridine (1.35 g), 10% palladium on carbon (containing water (50%), 0.675 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 hexane/THF to give the title compound (0.950 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 hexane/THF

Sources & evidence

ORD record
ord-fe3c802ea0744afcb8f364ef4e95e5d1
Source dataset
uspto-grants-2015_05
Patent number
US09029388B2

Reaction notes

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