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

HRID 1622591ノート

反応式

HRID 1622591 の反応式
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.[Cu](I)I>[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-27fd85981e934b6b9e3471cab1fc40f3
出典データセット
uspto-grants-2014_07
特許番号
US08778934B2

反応ノート

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