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

HRID 2191078ノート

反応式

HRID 2191078 の反応式
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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 7912Diisopropylamine溶媒

実験手順

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)−.

後処理

  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)

出典と根拠

ORDレコード
ord-96bb1b246ef1438bbb96cb715b821699
出典データセット
uspto-grants-2012_12
特許番号
US08324204B2

反応ノート

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