Acetic Acid → HCID 67013470, compound

HRID 42594Notes

Reaction equation

HRID 42594 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][CH2:31][O:32]C4CCCCO4)[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.CC(O)=O.C1COCC1.C([O-])(O)=O.[Na+]>O>[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][OH:32])[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

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 684439594,6-Bis(4-fluorophenyl)-5-(4-pyridyl)-2-[2-(tetrahydropiran-2-yloxy)ethyl]pyrazolo[3,4-b]pyridine

Product 1

HCID 67013470HCID 67013470, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4,6-bis(4-fluorophenyl)-5-(4-pyridyl)-2-[2-(tetrahydropyran-2-yloxy)ethyl]pyrazolo[3,4-b]pyridine (1.08 g, 2.09 mmol, obtained in example 24) in a 4:2:1 mixture of AcOH:THF:H2O (42 mL) was heated to 55° C. overnight. The mixture was allowed to cool and basified with saturated NaHCO3 and 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 hexane-EtOAc mixtures of increasing polarity as eluent, to afford 0.78 g of the title compound (yield: 87%).

Workup

  1. temperatureto cool
  2. extractionextracted with EtOAc
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. customThe crude product obtained
  6. customwas purified by chromatography on silica gel
  7. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-403b13765dc24805b8c3eb06801308a8
Source dataset
uspto-grants-2013_09
Patent number
US08536194B2

Reaction notes

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