1,4-Cyclohexadiene → 3-(1H-Pyrazol-4-yl)-5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine

HRID 1774985Notes

Reaction equation

HRID 1774985 reaction equation
C([N:8]1[CH:12]=[C:11]([C:13]2[C:21]3[C:16](=[CH:17][N:18]=[C:19]([C:22]4[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=4)[CH:20]=3)[N:15]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][O:29]3)[N:14]=2)[CH:10]=[N:9]1)C1C=CC=CC=1.C1CC=CCC=1>[OH-].[OH-].[Pd+2]>[NH:8]1[CH:12]=[C:11]([C:13]2[C:21]3[C:16](=[CH:17][N:18]=[C:19]([C:22]4[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=4)[CH:20]=3)[N:15]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][O:29]3)[N:14]=2)[CH:10]=[N:9]1

Participants

4

Reactant 2

HCID 123431,4-CyclohexadieneHCID 712536723-(1-Benzyl-1H-pyrazol-4-yl)-5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 1363339823-(1H-Pyrazol-4-yl)-5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridineYield 56.7%

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

A mixture of 234 mg (0.54 mmol) of 3-(1-benzyl-1H-pyrazol-4-yl)-5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine, 3.0 ml (32 mmol) of 1,4-cyclohexadiene and 400 mg of 20% palladium hydroxide on carbon was heated to reflux for 8 hours. The mixture was filtered, the filtrate concentrated in vacuum to afford 106 mg (31%) of 3-(1H-Pyrazol-4-yl)-5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine over three steps. ESI MS m/z 347.1 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 8 hours
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate concentrated in vacuum

Sources & evidence

ORD record
ord-b8dbcae2fd024491bce4c27b7eaff38c
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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