HCID 58495644, compound → HCID 58495654, compound

HRID 1190995Notes

Reaction equation

HRID 1190995 reaction equation
[CH:1]1([C:7]#[C:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]#[N:16])=[N:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CCOC(C)=O>[CH:1]1(/[CH:7]=[CH:8]\[C:9]2[CH:10]=[CH:11][C:12]([C:15]#[N:16])=[N:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 58495644HCID 58495644, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 58495654HCID 58495654, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Add 5-cyclohexylethynyl-pyridine-2-carbonitrile (1.4 g, 4.16 mmol) and Lindlar's Catalyst (0.5 g) to EtOAc (20 mL). Bubble hydrogen (via balloon) through the mixture for 2 h and stir under static atmosphere of hydrogen overnight. Filter the catalyst through Celite® and concentrate the filtrate in vacuo. Purify by chromatography on silica gel (80 g, pre-packed cartridge) eluting with hexane/EtOAc (1:0 to 9:1 gradient over 1.25 h, 80 mL/min) to obtain the desired intermediate as a colorless oil (0.89 g, 80%). MS (APCI+) m/z: 213 (M+H)+.

Workup

  1. filtrationFilter the catalyst through Celite®
  2. concentrationconcentrate the filtrate in vacuo
  3. customPurify by chromatography on silica gel (80 g, pre-packed cartridge)
  4. washeluting with hexane/EtOAc (1:0 to 9:1 gradient over 1.25 h, 80 mL/min)

Sources & evidence

ORD record
ord-1f4287dd2b154f49b9954b767c0d2fe1
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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