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Triethylamine → 5-Fluoro-3-((trimethylsilyl)ethynyl)pyridin-2-amine

HRID 490503
ノート
印刷プレビュー

反応式

HRID 490503 の反応式
[C:1]([Si:3]([CH3:6])([CH3:5])[CH3:4])#[CH:2].[Cl-].[Li+].C(N(CC)CC)C.[F:16][C:17]1[CH:18]=[C:19](I)[C:20]([NH2:23])=[N:21][CH:22]=1>CN(C)C=O.[Cu](I)I.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:16][C:17]1[CH:18]=[C:19]([C:2]#[C:1][Si:3]([CH3:6])([CH3:5])[CH3:4])[C:20]([NH2:23])=[N:21][CH:22]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 433294Lithium ChlorideHCID 184559742-Amino-5-fluoro-3-iodopyridine

生成物 1

HCID 597068495-Fluoro-3-((trimethylsilyl)ethynyl)pyridin-2-amine

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒
HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
55 °C

実験手順

12.47 cm3 of ethynyltrimethylsilane, 2.24 g of copper iodide, 2.74 g of lithium chloride, 41.33 cm3 of triethylamine and 2.15 g of [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride are added to a solution of 14 g of 5-fluoro-3-iodo-pyrid-2-ylamine in 440 cm3 of dimethylformamide, degassed with argon. The solution obtained is maintained at a temperature in the region of 55° C. for about 5 hours. After cooling to a temperature in the region of 20° C., the mixture is concentrated under reduced pressure (13 kPa); the residue is taken up in 300 cm3 of water and extracted with three times 100 cm3 of ethyl acetate. The combined organic phases are washed with three times 100 cm3 of water, dried over magnesium sulfate, filtered and concentrated under reduced pressure (13 kPa). 7.91 g of 5-fluoro-3-trimethylsilanylethynylpyrid-2-ylamine are thus obtained, after flash chromatography on a column of silica (eluent; dichloromethane), in the form of a solid, the characteristics of which are as follows:

後処理

  1. customdegassed with argon
  2. customThe solution obtained
  3. temperatureAfter cooling to a temperature in the region of 20° C.
  4. concentrationthe mixture is concentrated under reduced pressure (13 kPa)
  5. extractionextracted with three times 100 cm3 of ethyl acetate
  6. washThe combined organic phases are washed with three times 100 cm3 of water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure (13 kPa)

出典と根拠

ORDレコード
ord-92987fe74a664443a5753eac8406e32c
出典データセット
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07528147B2

反応ノート

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