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

HRID 1747859
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인쇄 미리보기

반응식

HRID 1747859 반응식
[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]
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참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6624273cb0194dcb89b3365052350875
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09150591B2

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