Ethyl 3-{4-(1-ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenyl}-3-(1-[{2-(trimethylsilyl)ethoxy}methyl]-1H-benzo[d]imidazol-2-yl)acrylate → Ethyl 3-[4-(1-ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenyl]-3-(1-[{2-(trimethylsilyl)ethoxy}methyl]-1H-benzo[d]imidazol-2-yl)propanoate

HRID 573299Notes

Reaction equation

HRID 573299 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([C:25]3[N:29]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:28]4[CH:38]=[CH:39][CH:40]=[CH:41][C:27]=4[N:26]=3)=[CH:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:14][CH:13]=2)=[N:4]1)[CH3:2]>CCO.[Pd]>[CH2:1]([N:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:13]=[CH:14][C:15]([CH:18]([C:25]3[N:29]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:28]4[CH:38]=[CH:39][CH:40]=[CH:41][C:27]=4[N:26]=3)[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:17]=2)=[N:4]1)[CH3:2]

Participants

4

Reactant 1

HCID 131732832Ethyl 3-{4-(1-ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenyl}-3-(1-[{2-(trimethylsilyl)ethoxy}methyl]-1H-benzo[d]imidazol-2-yl)acrylate

Product 1

HCID 86688972Ethyl 3-[4-(1-ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenyl]-3-(1-[{2-(trimethylsilyl)ethoxy}methyl]-1H-benzo[d]imidazol-2-yl)propanoateYield 90.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-[4-(1-ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenyl]-3-(1-[{2-(trimethylsilyl)ethoxy}methyl]-1H-benzo[d]imidazol-2-yl)acrylate (100 mg) and 10% Pd—C (18.74 mg) in EtOH (10 mL) was hydrogenated under balloon pressure at room temperature overnight. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to give the title compound (91 mg).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8b8fb5b52a804a04b8863b81f9fe5fa3
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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