Trimethylsilylacetylene → 5-Chloro-3-((trimethylsilyl)ethynyl)pyridin-2-amine

HRID 490449

반응식

HRID 490449 반응식
[Cl:1][C:2]1[CH:3]=[C:4](I)[C:5]([NH2:8])=[N:6][CH:7]=1.[C:10]([Si:12]([CH3:15])([CH3:14])[CH3:13])#[CH:11].[Cl-].[Li+]>C(N(CC)CC)C.CN(C)C=O.[Cu](I)I>[Cl:1][C:2]1[CH:3]=[C:4]([C:11]#[C:10][Si:12]([CH3:15])([CH3:14])[CH3:13])[C:5]([NH2:8])=[N:6][CH:7]=1

참가 물질

7

반응물 3

HCID 66111TrimethylsilylacetyleneHCID 433294Lithium ChlorideHCID 110760102-Amino-5-chloro-3-iodopyridine

생성물 1

HCID 247294655-Chloro-3-((trimethylsilyl)ethynyl)pyridin-2-amine

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

반응 조건

온도
40 °C

실험 절차

A suspension of 2.54 g of 5-chloro-3-iodopyridin-2-ylamine, 2.12 ml of ethynyltrimethylsilane, 0.38 g of copper iodide and 0.47 g of lithium chloride in 7 ml of triethylamine and 75 ml of dimethylformamide is degassed under argon for approximately 15 minutes. 0.408 g of [1,1′-bis(diphenylphosphino)ferrocene] palladium(II) chloride is added to the above suspension. The mixture is heated at around 40° C. for approximately 19 hours and then concentrated to dryness under reduced pressure (13 kPa). The residue is taken up with 50 ml of water, and extracted with three times 100 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered, and concentrated to dryness under reduced pressure (13 kPa). The residue is purified by flash chromatography on a silica column [eluent: cyclohexane/ethyl acetate (70/30 by volume)]. 1.63 g of 5-chloro-3-trimethylsilanylethynylpyridin-2-ylamine are obtained in the form of a solid, the characteristics of which are as follows:

후처리

  1. customis degassed under argon for approximately 15 minutes
  2. addition0.408 g of [1,1′-bis(diphenylphosphino)ferrocene] palladium(II) chloride is added to the above suspension
  3. concentrationconcentrated to dryness under reduced pressure (13 kPa)
  4. extractionextracted with three times 100 ml of ethyl acetate
  5. dry with materialThe combined organic phases are dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (13 kPa)
  8. customThe residue is purified by flash chromatography on a silica column [eluent: cyclohexane/ethyl acetate (70/30 by volume)]

출처 및 근거

ORD 기록
ord-89142a96ad574f4d82569bd0039d3036
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528147B2

연결된 노트

불러오는 중…