Cyclohexene → HCID 178469270, compound

HRID 1486240Notes

Reaction equation

HRID 1486240 reaction equation
C([O:8][C:9]1[N:14]2[N:15]=[C:16]([CH3:23])[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:13]2[CH:12]=[C:11]([CH3:24])[CH:10]=1)C1C=CC=CC=1.C1CCCCC=1>C(O)C.[Pd]>[OH:8][C:9]1[N:14]2[N:15]=[C:16]([CH3:23])[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:13]2[CH:12]=[C:11]([CH3:24])[CH:10]=1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 117859771Ethyl 7-(benzyloxy)-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylate

Product 1

HCID 178469270HCID 178469270, compoundYield 85.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2 g (5.98 mmol) of ethyl 7-(benzyloxy)-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylate from Example 7A were initially charged in 80 ml of ethanol under argon, and 636 mg (0.59 mmol, 10%) of palladium on activated carbon and 18 ml (179.42 mmol) of cyclohexene were added. The reaction mixture was stirred under reflux for 2.5 hours. Then the reaction mixture was filtered through kieselguhr and washed with ethanol, and the filtrate was concentrated. The residue was taken up in DMSO and acetonitrile and purified by means of preparative HPLC (RP 18 column, eluent:acetonitrile/water gradient with addition of 0.1% TFA). The product fractions were combined, concentrated and lyophilized. 1.2 g of the target compound were obtained (86% of theory).

Workup

  1. temperatureunder reflux for 2.5 hours
  2. filtrationThen the reaction mixture was filtered through kieselguhr
  3. washwashed with ethanol
  4. concentrationthe filtrate was concentrated
  5. customacetonitrile and purified by means of preparative HPLC (RP 18 column, eluent:acetonitrile/water gradient with addition of 0.1% TFA)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ae4037f59cc44faa8528da88047bdae3
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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