5-(Oct-1-ynyl)-1H-indole → 5-octyl-1H-indole

HRID 710287

反応式

HRID 710287 の反応式
[C:1]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]>CCO.[Pd].[C]>[CH2:1]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

参加物

4

反応物 1

HCID 667267515-(Oct-1-ynyl)-1H-indole

生成物 1

HCID 667262575-octyl-1H-indole収率 46.5%

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 702Ethanol溶媒

実験手順

A mixture of the product of Step A (0.17 g; 0.75 mmol) and 10% Pd/carbon (0.2 g) in EtOH (15 ml) was stirred at room temperature for 40 min under H2 (balloon). The catalyst was removed by filtration through the Celite pad, washed with CH2Cl2 (2×10 ml) and combined filtrates were evaporated to dryness under reduced pressure. The residue was purified by FCC (SiO2; hexane/EtOAc; 9:1) to give the title compound (0.08 g; 46%) as a colourless syrup. 1H-NMR (CDCl3) 0.86 (tr, 3H, J=6.7 Hz); 1.28 (m, 10H); 1.65 (m, 2H); 2.68 (tr, 2H, J=7.9 Hz); 6.47 (m, 1H); 7.02 (dd, 1H, J=1.5, 8.3 Hz); 7.16 (m, 1H); 7.29 (d, 1H, J=8.3 Hz); 7.42 (s, 1H); 8.04 (broad s, 1H).

後処理

  1. customThe catalyst was removed by filtration through the Celite pad
  2. washwashed with CH2Cl2 (2×10 ml)
  3. customwere evaporated to dryness under reduced pressure
  4. customThe residue was purified by FCC (SiO2; hexane/EtOAc; 9:1)

出典と根拠

ORDレコード
ord-d6ac4178d54e45dc807d3c7923865d7a
出典データセット
uspto-grants-2015_11
特許番号
US09181182B2

関連ノート

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