Methyl iodide → 5-Chloro-1-methylindole

HRID 226012

反応式

HRID 226012 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[H-].[Na+].I[CH3:14]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:14])[CH:6]=[CH:5]2

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 871105-Chloroindole

生成物 1

HCID 108558435-Chloro-1-methylindole収率 50%

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, 1.00 g (6.60 mmol) of 5-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. 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 0.545 g of the title compound, 50% yield. MS, ES=166.0 (M+1); 1H NMR (DMSO-d6) δ 7.567-7.564 (m, 1H); 7.453-7.431 (m, 1H); 7.381-7.374 (m, 1H); 7.131-7.105 (m, 1H); 6.393-6.386 (m, 1H); 2.768 (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-5e7e22003c874d43811f9a9cf1ff48a9
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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