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

HRID 710287

반응식

HRID 710287 반응식
[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]

참가 물질

4

반응물 1

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

생성물 1

HCID 667262575-octyl-1H-indole수율 46.5%

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 702Ethanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d6ac4178d54e45dc807d3c7923865d7a
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181182B2

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