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

HRID 222476

反応式

HRID 222476 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 31268Pyrrolidine溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5f53458e1c2e44e08097bb9e3561dbbe
出典データセット
uspto-grants-2012_06
特許番号
US08207216B2

関連ノート

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