HCID 86676042, compound → HCID 71236317, compound

HRID 2369731Notes

Reaction equation

HRID 2369731 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH3:22])=[CH2:21])=[CH:16][N:15]=2)=[CH:3][CH:2]=1>[Pd].[Pt].CCO>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]([CH3:22])[CH3:21])=[CH:16][N:15]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 1

HCID 86676042HCID 86676042, compound

Product 1

HCID 71236317HCID 71236317, compoundYield 99.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

2-(Dibenzo[b,d]furan-4-yl)-5-(prop-1-en-2-yl)pyridine (7.5 g, 26.3 mmol) was added to a hydrogenator bottle containing EtOH (150 mL). The reaction mixture was degassed by bubbling nitrogen for 10 min. Pd/C (0.28 g, 2.63 mmol) and Pt/C (0.26 g, 1.3 mmol) were added to the reaction mixture. The reaction mixture was placed on the Parr hydrogenator for 1 h. The reaction mixture was filtered on a tightly packed Celite® bed and washed with dichloromethane to yield 7.5 g (99%) of the desired product. The product was confirmed by GC/MS and NMR.

Workup

  1. customThe reaction mixture was degassed
  2. customby bubbling nitrogen for 10 min
  3. filtrationThe reaction mixture was filtered on a tightly packed Celite® bed
  4. washwashed with dichloromethane

Sources & evidence

ORD record
ord-96e48cbc1abb41aa92959c3a2313025d
Source dataset
uspto-grants-2014_04
Patent number
US08709615B2

Reaction notes

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