Trifluoroacetic acid → 4,6-Bis(4-fluorophenyl)-2-(4-piperidyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine

HRID 42575Notes

Reaction equation

HRID 42575 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:22]=[C:21]3[C:16]([N:17]=[C:18]([C:36]4[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=4)[C:19]([C:30]4[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=4)=[C:20]3[C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)=[N:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:29][C:26]1[CH:27]=[CH:28][C:23]([C:20]2[C:21]3[C:16](=[N:15][N:14]([CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]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

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 684430892-[1-(Tert-butoxycarbonyl)piperidin-4-yl]-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine

Product 1

HCID 670147574,6-Bis(4-fluorophenyl)-2-(4-piperidyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridineYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[1-(tert-butoxycarbonyl)piperidin-4-yl]-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine (0.62 g, 1.1 mmol, obtained in example 20) in CH2Cl2 (19 mL) under argon atmosphere and cooled to 0° C., trifluoroacetic acid (1.8 mL) was added. It was stirred at room temperature for 2.5 h. The solvent was evaporated. The residue was dissolved in CHCl3 and washed with 1 N NaOH and brine. The organic phase was dried over Na2SO4 and concentrated to dryness, to afford 319 mg of the title compound (yield: 62%).

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in CHCl3
  3. washwashed with 1 N NaOH and brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c429a453f5884a26af87b817997a4b9b
Source dataset
uspto-grants-2013_09
Patent number
US08536194B2

Reaction notes

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