(Triethylsilyl)acetylene → 5-[(Triethylsilyl)ethynyl]-1H-indole

HRID 2191078노트

반응식

HRID 2191078 반응식
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH2:11]([Si:13]([C:18]#[CH:19])([CH2:16][CH3:17])[CH2:14][CH3:15])[CH3:12]>C(NC(C)C)(C)C.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.[Cu]I>[CH2:14]([Si:13]([C:11]#[C:12][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2)([CH2:18][CH3:19])[CH2:16][CH3:17])[CH3:15]

참가 물질

6

반응물 2

HCID 637947(Triethylsilyl)acetyleneHCID 27823135-Iodo-1H-indole

생성물 1

HCID 668932335-[(Triethylsilyl)ethynyl]-1H-indole수율 101.8%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 7912Diisopropylamine용매

실험 절차

To a stirred solution of 5-iodoindole (0.50 g, 2.0 mmol) and (triethylsilyl)-acetylene (0.58 g, 4.0 mmol) in diisopropylamine (15 mL) was added Pd(PPh3)2Cl2 (0.07 g, 0.10 mmol) and CuI (0.04 g, 0.20 mmol) and the reaction mixture was stirred at r.t. for 16 h. The solvent was then removed in vacuo. EtOAc (15 mL) and water (15 mL) were added and the layers separated. The aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layers were washed with water (2×20 mL), dried (Na2SO4), filtered and concentrated in vacuo. Purification by column chromatography (SiO2, 10% EtOAc/hexanes) gave the title compound (0.52 g, quantitative). δH (DMSO-d6) 11.30 (1H, br. s), 7.69 (1H, s), 7.45-7.41 (1H, m), 7.37 (1H, d, J 8.4 Hz), 7.15 (1H, dd, J 8.4 and 1.5 Hz), 6.48-6.40 (1H, m), 1.02 (9H, t, J 7.8 Hz), 0.65 (6H, q, J 7.9 Hz). MS (ES−) 254.0 (M−H)−.

후처리

  1. customThe solvent was then removed in vacuo
  2. additionEtOAc (15 mL) and water (15 mL) were added
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
  5. washThe combined organic layers were washed with water (2×20 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by column chromatography (SiO2, 10% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-96bb1b246ef1438bbb96cb715b821699
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324204B2

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