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

HRID 1747858Notes

Reaction equation

HRID 1747858 reaction equation
Br[C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:9]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=1)#[CH:10].O>C(N(CC)CC)C>[CH3:19][CH:17]([C:14]1[CH:13]=[CH:12][C:11]([C:9]#[C:10][C:2]2[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][CH:7]=2)=[CH:16][CH:15]=1)[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 6375011-Ethynyl-4-(1-methylethyl)benzeneHCID 8177002-Amino-3-bromopyridine

Product 1

HCID 667477103-{[4-(1-Methylethyl)phenyl]ethynyl}pyridin-2-amineYield 46.6%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of bis(triphenylphosphine)palladium(0)dichloride (0.811 g), 3-bromopyridin-2-amine (2 g), 1-ethynyl-4-isopropylbenzene (1.667 g) and copper iodide(I) (0.22 g) in triethylamine (38.6 mL) was heated under reflux. Water was added to the reaction mixture, the mixture was filtered through celite, and the filtrate 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 (1273 mg) as a pale-yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. filtrationthe mixture was filtered through celite
  4. extractionthe filtrate was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0b9805c90ede40feac502db77733791a
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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