Ethyl Acetate → 2-(4,4-Difluoro-piperidine-1-carbonyl)-5-hydroxy-pyrrolo[2,3-b]pyridine-1-carboxylic Acid tert-butyl Ester

HRID 1437699Notes

Reaction equation

HRID 1437699 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2=[N:13][CH:14]=[C:15]([O:17]CC3C=CC=CC=3)[CH:16]=[C:11]2[CH:10]=[C:9]1[C:25]([N:27]1[CH2:32][CH2:31][C:30]([F:34])([F:33])[CH2:29][CH2:28]1)=[O:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C>CO>[C:1]([O:5][C:6]([N:8]1[C:12]2=[N:13][CH:14]=[C:15]([OH:17])[CH:16]=[C:11]2[CH:10]=[C:9]1[C:25]([N:27]1[CH2:32][CH2:31][C:30]([F:34])([F:33])[CH2:29][CH2:28]1)=[O:26])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 684261195-Benzyloxy-2-(4,4-difluoro-piperidine-1-carbonyl)-pyrrolo[2,3-b]pyridine-1-carboxylic Acid tert-butyl Ester

Product 1

HCID 684239772-(4,4-Difluoro-piperidine-1-carbonyl)-5-hydroxy-pyrrolo[2,3-b]pyridine-1-carboxylic Acid tert-butyl EsterYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of 0.3 g (0.64 mmol) 5-benzyloxy-2-(4,4-difluoro-piperidine-1-carbonyl)-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester in 3 ml methanol and 4 ml ethyl acetate 45 mg palladium on activated charcoal (10%) was added and the suspension was hydrogenated at 1.3 bar for 15 min. The suspension was filtered over Dicalite Speed Plus®(Aldrich), the filtercake was washed with ethyl acetate and methanol and the filtrate evaporated. The residue was purified by flash column chromatography on silica gel with ethyl acetate:n-heptane (2:1) as eluant to give 0.19 g (78%) of the desired compound as a colorless solid.

Workup

  1. filtrationThe suspension was filtered over Dicalite Speed Plus®(Aldrich)
  2. washthe filtercake was washed with ethyl acetate and methanol
  3. customthe filtrate evaporated
  4. customThe residue was purified by flash column chromatography on silica gel with ethyl acetate:n-heptane (2:1) as eluant

Sources & evidence

ORD record
ord-9ec1efaf2c23473598938c5921125075
Source dataset
uspto-grants-2009_11
Patent number
US07622466B2

Reaction notes

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