3-{[4-(1-Methylethyl)phenyl]ethynyl}pyridin-2-amine → 3-{2-[4-(1-Methylethyl)phenyl]ethyl}pyridin-2-amine

HRID 1405658Notes

Reaction equation

HRID 1405658 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[C:13]([NH2:18])=[N:14][CH:15]=[CH:16][CH:17]=2)=[CH:6][CH:5]=1)[CH3:3]>CO.[C].[Pd]>[CH3:3][CH:2]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][C:12]2[C:13]([NH2:18])=[N:14][CH:15]=[CH:16][CH:17]=2)=[CH:8][CH:9]=1)[CH3:1]

Participants

4

Reactant 1

HCID 667477103-{[4-(1-Methylethyl)phenyl]ethynyl}pyridin-2-amine

Product 1

HCID 641350373-{2-[4-(1-Methylethyl)phenyl]ethyl}pyridin-2-amineYield 36.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of 10% palladium-carbon (50% wet, 50 mg) and 3-{[4-(1-methylethyl)phenyl]ethynyl}pyridin-2-amine (662.8 mg) in methanol (15 mL) was stirred under a hydrogen atmosphere at room temperature for 3 hr. The reaction mixture was filtered, a saturated aqueous sodium hydrogen carbonate solution was added to the filtrate, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (246.6 mg) as a colorless oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additiona saturated aqueous sodium hydrogen carbonate solution was added to the filtrate
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8d7790ba832e45f8a581a7df135338c9
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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