Methyl iodide → 4-Chloro-1-methyl-1H-indole

HRID 226011

反応式

HRID 226011 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[H-].[Na+].IC.[C:15](OCC)(=O)C>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[CH3:15]

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 913454-Chloroindole

生成物 1

HCID 130487594-Chloro-1-methyl-1H-indole収率 72%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

In an oven dried, nitrogen purged, 3 neck, 50 mL round bottom flask, 0.794 mL (6.60 mmol) of 4-chloroindole in 10 mL of dry dimethylformamide is reacted with 0.260 g (6.60 mmol) of 60% sodium hydride dispersed in mineral oil at room temperature for 4 h. 0.411 mL (6.60 mmol) of iodomethane is added and the reaction is allowed to stir at room temperature 15 h. TLC (2:1 hexanes:ethyl acetate) indicates the starting material is gone and new less polar spot. The reaction is quenched with 50 mL of water, extracted 3×50 mL of ethyl acetate, dried (MgSO4), and concentrated. The crude product is purified by chromatography using hexanes:ethyl acetate as a solvent system to obtain 0.785 g of the title compound, 72% yield. MS, ES=166.1 (M+1); 1H NMR (DMSO-d6) δ 7.431-7.413 (m, 2H); 7.145-7.064 (m, 2H); 6.442-6.432 (m, 1H); 3.795 (s, 3H) ppm.

後処理

  1. customIn an oven dried
  2. customnitrogen purged
  3. additiondispersed in mineral oil at room temperature for 4 h
  4. customThe reaction is quenched with 50 mL of water
  5. extractionextracted 3×50 mL of ethyl acetate
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe crude product is purified by chromatography

出典と根拠

ORDレコード
ord-4d54fea55d5d4b67b790ba7adf47fbd9
出典データセット
uspto-grants-2009_07
特許番号
US07557103B2

関連ノート

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