HCID 89713714, compound → HCID 89713652, compound

HRID 1518979Notes

Reaction equation

HRID 1518979 reaction equation
[CH:1]1([CH:5]2[CH:10]=[CH:9][N:8]([C:11]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:12])[CH:7]=[CH:6]2)[CH2:4][CH2:3][CH2:2]1>[Pd].CO>[CH:1]1([CH:5]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:12])[CH2:7][CH2:6]2)[CH2:2][CH2:3][CH2:4]1

Participants

4

Reactant 1

HCID 89713714HCID 89713714, compound

Product 1

HCID 89713652HCID 89713652, compoundYield 51.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

Charge a 500 mL Parr reactor bottle with 10% palladium on carbon (0.56 g, 0.53 mmol) and purge with N2. Wet the catalyst with MeOH (50 mL) and add phenyl 4-cyclobutylpyridine-1(4H)-carboxylate (5.6 g, 21.9 mmol) and an additional 150 mL MeOH. Seal the bottle, purge four times with nitrogen, then four times with hydrogen. Pressurize with hydrogen gas (31 psi) and shake at ambient temperature for two hours. Vent the mixture, purge four times with nitrogen, filter the mixture; collect the filtrate; and then concentrate to remove the MeOH. Purify the crude material with silica gel flash column chromatography eluting with 10% EtOAc in hexane. Concentrate the fractions to give the title compound (2.93 g, 51.5%). MS (m/z): 260.

Workup

  1. custompurge with N2
  2. customSeal the bottle
  3. custompurge four times with nitrogen
  4. customVent the mixture, purge four times with nitrogen
  5. filtrationfilter the mixture
  6. customcollect the filtrate
  7. concentrationand then concentrate
  8. customto remove the MeOH
  9. customPurify the crude material with silica gel flash column chromatography
  10. washeluting with 10% EtOAc in hexane
  11. concentrationConcentrate the fractions

Sources & evidence

ORD record
ord-ab2cbb7e331d490ab66b06dbd53c22cc
Source dataset
uspto-grants-2015_07
Patent number
US09073856B2

Reaction notes

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