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

HRID 1916707

반응식

HRID 1916707 반응식
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]

참가 물질

7

반응물 2

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

생성물 1

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

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-5f39630562004788afc88eab2ed230ba
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618132B2

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