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

HRID 1405657노트

반응식

HRID 1405657 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-71c0aa404072477e8935ded0b21a539f
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916551B2

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