Formic Acid → HCID 67014607, compound

HRID 2376784Notes

Reaction equation

HRID 2376784 reaction equation
C([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][N:14]1[CH:22]=[C:21]2[C:16]([N:17]=[C:18]([C:36]3[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=3)[C:19]([C:30]3[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=3)=[C:20]2[C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[N:15]1)C1C=CC=CC=1.C(O)=O>CCO.[Pd]>[F:29][C:26]1[CH:27]=[CH:28][C:23]([C:20]2[C:21]3[C:16](=[N:15][N:14]([CH2:13][CH:9]4[CH2:10][CH2:11][CH2:12][NH:8]4)[CH:22]=3)[N:17]=[C:18]([C:36]3[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=3)[C:19]=2[C:30]2[CH:31]=[CH:32][N:33]=[CH:34][CH:35]=2)=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 670148852-(1-Benzylpyrrolidin-2-ylmethyl)-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine

Product 1

HCID 67014607HCID 67014607, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-(1-benzylpyrrolidin-2-ylmethyl)-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine (83 mg, 0.1 mmol, obtained in example 259) in EtOH (6.9 mL), 10% Pd/C (8 mg) and formic acid (0.34 mL) were added and heated a reflux for 2 h. It was allowed to cool and filtered through celite, washed with EtOH and concentrated. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc-MeOH—NH3 of increasing polarity as eluent, to afford 40 mg of the title compound (yield: 57%)

Workup

  1. temperatureheated
  2. temperaturea reflux for 2 h
  3. temperatureto cool
  4. filtrationfiltered through celite
  5. washwashed with EtOH
  6. concentrationconcentrated
  7. customThe crude product obtained
  8. customwas purified by chromatography on silica gel
  9. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-e9553053cf1842879327c3788adc4ee1
Source dataset
uspto-grants-2008_12
Patent number
US07468376B2

Reaction notes

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