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

HRID 490449

反応式

HRID 490449 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

反応条件

温度
40 °C

実験手順

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:

後処理

  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)]

出典と根拠

ORDレコード
ord-89142a96ad574f4d82569bd0039d3036
出典データセット
uspto-grants-2009_05
特許番号
US07528147B2

関連ノート

読み込み中…