7-(benzyloxy)-5-(3,4-dimethoxyphenyl)-1-methyl-1H-benzo[d]imidazole → 5-(3,4-dimethoxyphenyl)-1-methyl-1H-benzo[d]imidazol-7-ol

HRID 2209020Notes

Reaction equation

HRID 2209020 reaction equation
C([O:8][C:9]1[C:14]2[N:15]([CH3:18])[CH:16]=[N:17][C:13]=2[CH:12]=[C:11]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=2)[CH:10]=1)C1C=CC=CC=1>C(O)C.[Pd]>[CH3:28][O:27][C:21]1[CH:20]=[C:19]([C:11]2[CH:10]=[C:9]([OH:8])[C:14]3[N:15]([CH3:18])[CH:16]=[N:17][C:13]=3[CH:12]=2)[CH:24]=[CH:23][C:22]=1[O:25][CH3:26]

Participants

4

Reactant 1

HCID 1178441327-(benzyloxy)-5-(3,4-dimethoxyphenyl)-1-methyl-1H-benzo[d]imidazole

Product 1

HCID 1178435835-(3,4-dimethoxyphenyl)-1-methyl-1H-benzo[d]imidazol-7-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent2×

Procedure

To a solution of 7-(benzyloxy)-5-(3,4-dimethoxyphenyl)-1-methyl-1H-benzo[d]imidazole 2.52 (106 mg) in ethanol (4 mL) was added Pd/C (10% wet). The mixture was stirred at 1 atm H2 overnight. LCMS showed some starting material was still remaining, another 50 mg of Pd/C (10% wet) was added and after 1 h under H2 (balloon), the reaction mixture was diluted with ethanol and filtered through celite and washed with ethanol. The filtrate was then concentrated and purified by flash chromatography (SiO2, 1% MeOH/EtOAc to 30% MeOH/EtOAc) to afford 5-(3,4-dimethoxyphenyl)-1-methyl-1H-benzo[d]imidazol-7-ol 2.53.

Workup

  1. filtrationfiltered through celite
  2. washwashed with ethanol
  3. concentrationThe filtrate was then concentrated
  4. custompurified by flash chromatography (SiO2, 1% MeOH/EtOAc to 30% MeOH/EtOAc)

Sources & evidence

ORD record
ord-dfb29e65c2c94ed396714b5828f982a4
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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