Piperidin-4-ol → 1-[2-[4,6-Bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridin-2-yl]ethyl]piperidin-4-ol

HRID 42597Notes

Reaction equation

HRID 42597 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:10](=[N:27][N:28]([CH2:30][CH:31]=O)[CH:29]=3)[N:11]=[C:12]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH:47][CH:48]1[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]1>ClCCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:10](=[N:27][N:28]([CH2:30][CH2:31][N:51]4[CH2:52][CH2:53][CH:48]([OH:47])[CH2:49][CH2:50]4)[CH:29]=3)[N:11]=[C:12]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[C:13]=2[C:14]2[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 79341Piperidin-4-olHCID 5049666Sodium triacetoxyborohydrideHCID 86606798HCID 86606798, compound

Product 1

HCID 684448031-[2-[4,6-Bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridin-2-yl]ethyl]piperidin-4-olYield 20%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In a volumetric flask, 2-[4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridin-2-yl]acetaldehyde (0.08 g, 0.2 mmol, obtained in example 94), sodium triacetoxyborohydride (0.08 g, 0.4 mmol), 4-hydroxypiperidine (0.02 g, 0.2 mmol) and 1,2-dichloroethane (3 mL) were introduced under argon atmosphere. The mixture was stirred overnight at room temperature. It was concentrated and a mixture of water and EtOAc were added. The phases were separated. The aqueous phase was extracted with EtOAc. The organic phase was dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using increasing polarity mixtures of EtOAc-MeOH as eluent, to afford 19 mg of the title compound (yield: 20%).

Workup

  1. concentrationIt was concentrated
  2. additiona mixture of water and EtOAc
  3. additionwere added
  4. customThe phases were separated
  5. extractionThe aqueous phase was extracted with EtOAc
  6. dry with materialThe organic phase was dried over Na2SO4
  7. concentrationconcentrated to dryness
  8. customThe crude product obtained
  9. customwas purified by chromatography on silica gel using
  10. temperatureincreasing polarity mixtures of EtOAc-MeOH as eluent

Sources & evidence

ORD record
ord-8683444f98bd490394db1a7f10619b5c
Source dataset
uspto-grants-2013_09
Patent number
US08536194B2

Reaction notes

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