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Trimethylsilylacetylene → 2-(5-trimethylsilylethynyl-3-pyridyloxy)-N-(4-methylpent-2-yn-4-yl)butyramide

HRID 1374920
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HRID 1374920 반응식
Br[C:2]1[CH:3]=[C:4]([O:8][CH:9]([CH2:19][CH3:20])[C:10]([NH:12][C:13]([CH3:18])([CH3:17])[C:14]#[C:15][CH3:16])=[O:11])[CH:5]=[N:6][CH:7]=1.[CH3:21][Si:22]([C:25]#[CH:26])([CH3:24])[CH3:23]>C(N(CC)CC)C.C(OCC)C.[Cu]Cl>[CH3:21][Si:22]([C:25]#[C:26][C:2]1[CH:3]=[C:4]([O:8][CH:9]([CH2:19][CH3:20])[C:10]([NH:12][C:13]([CH3:18])([CH3:17])[C:14]#[C:15][CH3:16])=[O:11])[CH:5]=[N:6][CH:7]=1)([CH3:24])[CH3:23]
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참가 물질

6

반응물 2

HCID 66111Trimethylsilylacetylene2회HCID 21078374HCID 21078374, 화합물

생성물 1

HCID 210784012-(5-trimethylsilylethynyl-3-pyridyloxy)-N-(4-methylpent-2-yn-4-yl)butyramide

시약·촉매·용매 3

HCID 62652Cuprous chloride촉매HCID 3283Diethyl Ether용매HCID 8471
Triethylamine
용매

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온도
90 °C

실험 절차

2-(5-Bromo-3-pyridyloxy)-N-(4-methylpent-2-yn-4-yl)butyramide (0.40 g), trimethylsilylacetylene (0.24 ml), copper (I) chloride (0.015 g) and palladium dichloride bis(triphenyl)phosphine (0.030 g) in dry triethylamine (4 ml) were sealed in a glass tube and heated to 90° C. for 3 hours. The mixture was cooled to ambient temperature and stored for 18 hours. Further trimethylsilylacetylene (0.24 ml) and palladium dichloride bis(triphenyl)-phosphine (0.030 g) were added and the mixture re-heated in the sealed tube for another 5.5 hours. The reaction mixture was cooled to ambient temperature, stored for 72 hours, diluted with diethyl ether and washed with water (three times). The organic phase was separated, dried over magnesium sulphate and evaporated under reduced pressure to give a dark yellow gum, ca. 0.4 g, containing the required product, which was used in the next Stage without further purification.

후처리

  1. temperatureThe mixture was cooled to ambient temperature
  2. temperaturethe mixture re-heated in the sealed tube for another 5.5 hours
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. waitstored for 72 hours
  5. washwashed with water (three times)
  6. customThe organic phase was separated
  7. dry with materialdried over magnesium sulphate
  8. customevaporated under reduced pressure
  9. customto give a dark yellow gum, ca. 0.4 g

출처 및 근거

ORD 기록
ord-40abed4075dd486d9538de71bf5d5e8f
출처 데이터셋
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07166621B2

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