Trimethylsilylacetylene → 1-Methyl-5-trimethylsilanylethynyl-1H-indole

HRID 222476

반응식

HRID 222476 반응식
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[CH:5]2.[C:12]([Si:14]([CH3:17])([CH3:16])[CH3:15])#[CH:13]>N1CCCC1>[CH3:11][N:7]1[C:8]2[C:4](=[CH:3][C:2]([C:13]#[C:12][Si:14]([CH3:17])([CH3:16])[CH3:15])=[CH:10][CH:9]=2)[CH:5]=[CH:6]1

참가 물질

4

반응물 2

HCID 66111TrimethylsilylacetyleneHCID 113228355-iodo-1-methyl-1H-indole

생성물 1

HCID 591406701-Methyl-5-trimethylsilanylethynyl-1H-indole수율 84,794%

시약·촉매·용매 1

HCID 31268Pyrrolidine용매

반응 조건

온도
50 °C

실험 절차

To a solution of 5-iodo-1-methyl-1H-indole (200 mg, 0.778 mmol) in pyrrolidine (5 mL) was added ethynyl-trimethyl-silane (92 mg, 0.932 mmol), followed by tetrakis-triphenyl-phosphine palladium (61 mg, 0.233 mmol) after which the reaction mixture was heated at 50° C. for 12 h. The reaction mixture was filtered and the filtrate evaporated in vacuo to obtain a residue, which was purified by column chromatography (ethyl acetate:hexane; 5:95) to give a product (150 g, 84%). 1H NMR (CDCl3, 400 MHz) 0.25 (s, 9H), 3.76 (s, 3H), 6.44 (d, J=3.0 Hz, 1H), 7.04 (d, J=3.0 Hz, 1H), 7.23 (d, J=8.4 Hz, 1H), 7.30 (dd, J=1.4 Hz, 1H), 7.78 (d, J=1.4 Hz, 1H); 13C NMR (CDCl3, 100 MHz) 0.18, 32.8, 90.9, 101.2, 107.0, 109.0, 113.6, 125.3, 125.4, 128.1, 129.6, 136.4.

후처리

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate evaporated in vacuo
  3. customto obtain a residue, which
  4. customwas purified by column chromatography (ethyl acetate:hexane; 5:95)

출처 및 근거

ORD 기록
ord-5f53458e1c2e44e08097bb9e3561dbbe
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207216B2

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