1,4-Cyclohexadiene → HCID 71254190, compound

HRID 1775041Notes

Reaction equation

HRID 1775041 reaction equation
[C:1]1([C:6]2[C:14]3[C:9](=[CH:10][N:11]=[C:12]([C:15]4[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=4)[CH:13]=3)[N:8]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][O:22]3)[N:7]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1.C1CC=CCC=1>[Pd].C(O)C>[CH:1]1([C:6]2[C:14]3[C:9](=[CH:10][N:11]=[C:12]([C:15]4[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=4)[CH:13]=3)[N:8]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][O:22]3)[N:7]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 123431,4-Cyclohexadiene2×HCID 71253722HCID 71253722, compound

Product 1

HCID 71254190HCID 71254190, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 42 mg (0.12 mmol) of 3-cyclopentenyl-5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine, 2.0 ml (21 mmol) of 1,4-cyclohexadiene and 100 mg of 10% palladium on carbon in 10 ml of ethanol was heated to reflux for 48 hours, during which 1,4-cyclohexadiene was added incrementally. The mixture was filtered through celite, and the filtrate was concentrated to afford 31 mg (76%) of 3-Cyclopentyl-5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine. ESI MS m/z 349.2 (M+1).

Workup

  1. temperaturewas heated
  2. additionwas added incrementally
  3. filtrationThe mixture was filtered through celite
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-359e4a21967d41e98c357b63d9f7d35b
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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