(3-Benzyloxy-2-ethoxyphenyl)-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol → (2-ethoxy-3-hydroxy-phenyl)-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

HRID 1965016Notes

Reaction equation

HRID 1965016 reaction equation
C([O:8][C:9]1[C:10]([O:36][CH2:37][CH3:38])=[C:11]([CH:15]([C:17]2[C:25]3[C:20](=[N:21][CH:22]=[CH:23][CH:24]=3)[N:19]([Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])[CH:18]=2)[OH:16])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>CO.O1CCCC1.[Pd]>[CH2:37]([O:36][C:10]1[C:9]([OH:8])=[CH:14][CH:13]=[CH:12][C:11]=1[C:15]([C:17]1[C:25]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[N:19]([Si:26]([CH:30]([CH3:31])[CH3:32])([CH:27]([CH3:29])[CH3:28])[CH:33]([CH3:34])[CH3:35])[CH:18]=1)=[O:16])[CH3:38]

Participants

5

Reactant 1

HCID 66679415(3-Benzyloxy-2-ethoxyphenyl)-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol

Product 1

HCID 58086092(2-ethoxy-3-hydroxy-phenyl)-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanoneYield 95%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3-benzyloxy-2-ethoxy-phenyl)-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol (664, 195 mg, 0.37 mmol) in a mixture of methanol (20 mL) and tetrahydrofuran (50 mL) was added palladium on carbon (50 mg, 10% wt., 0.2 mmol). The mixture was stirred under hydrogenation for seventeen hours. After removal of solvent, the residue was washed with a mixture of ethyl ether and hexanes to provide the compound as a white solid (665, 63 mg, 95%). MS(ESI) [M+H+]+=439.37.

Workup

  1. customAfter removal of solvent
  2. washthe residue was washed with a mixture of ethyl ether and hexanes

Sources & evidence

ORD record
ord-f21aa803f50042a2897d19c57e27cb5f
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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