Trimethylsilylacetylene → 2-(5-Trimethylsilanylethynyl-indol-1-yl)-ethanol

HRID 1916707

反応式

HRID 1916707 の反応式
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][OH:13])[CH:6]=[CH:5]2.[C:14]([Si:16]([CH3:19])([CH3:18])[CH3:17])#[CH:15]>C(N(CC)CC)C.C1COCC1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:17][Si:16]([C:14]#[C:15][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][OH:13])[CH:6]=[CH:5]2)([CH3:19])[CH3:18]

参加物

7

反応物 2

HCID 66111TrimethylsilylacetyleneHCID 457893802-(5-Iodo-indol-1-yl)-ethanol

生成物 1

HCID 673645732-(5-Trimethylsilanylethynyl-indol-1-yl)-ethanol

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

反応条件

温度
0 °C

実験手順

398 mg (2.1 mmol) CuI and 1.47 g (2.1 mmol) Pd(PPh3)2Cl2 are added to a solution, cooled to 0° C., of 30 g (104 mmol) 2-(5-iodo-indol-1-yl)-ethanol and 18 mL (125 mmol) ethynyl-trimethyl-silane in 480 mL triethylamine and 120 mL THF and stirred for 30 min at 0° C. and 2 h at RT. The mixture is evaporated down i. vac., the residue is taken up in 300 mL EtOAc, the organic phase is washed with 150 mL water and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, gradient: cyc/EtOAc 4:1 to 2:1).

後処理

  1. customThe mixture is evaporated down i
  2. washthe organic phase is washed with 150 mL water
  3. dry with materialdried over Na2SO4
  4. customis purified by chromatography (silica gel, gradient: cyc/EtOAc 4:1 to 2:1)

出典と根拠

ORDレコード
ord-5f39630562004788afc88eab2ed230ba
出典データセット
uspto-grants-2013_12
特許番号
US08618132B2

関連ノート

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