Methyl iodide → Ethyl 1,2-dimethyl-1H-indole-3-carboxylate

HRID 642416

反応式

HRID 642416 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]=1[CH3:15])=[O:5])[CH3:2].[CH3:16]I.[H-].[Na+]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH3:16])[C:7]=1[CH3:15])=[O:5])[CH3:2]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 4072358ethyl 2-methyl-1H-indole-3-carboxylate

生成物 1

HCID 599139Ethyl 1,2-dimethyl-1H-indole-3-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To an ice-water bath cooled solution of 2-methyl-1H-indole-3-carboxylic acid ethyl ester (5.197 g, prepared according to Suzuki et al. (1984) Synthesis (Stuttgart) 7:616-617), MeI (2.07 mL) in DMF (25 mL) was added NaH (1.33 g, 60% purity in mineral oil) under nitrogen gas stream. The reaction was stirred for 10 min at 0° C. and 20 min at room temperature and then quenched with diluted HCl solution, diluted with ice/water to a volume of ˜200 mL; the mixture was cooled with ice/water bath and the solids were collected with filtration, washed with water, and dried under high vacuum to give the desired crude product (5.87 g) as loose brown to yellow solid. 1H NMR (200 MHz, CDCl3): δ (ppm)=8.14-8.0 (m, 1H), 7.3-7.1 (m, 3H), 4.38 (q, 2H, J=7.1 Hz), 3.69 (s, 3H), 2.77 (s, 3H), 1.45 (t, 3H, J=7.1 Hz).

後処理

  1. customquenched with diluted HCl solution
  2. additiondiluted with ice/water to a volume of ˜200 mL
  3. temperaturethe mixture was cooled with ice/water bath
  4. filtrationthe solids were collected with filtration
  5. washwashed with water
  6. customdried under high vacuum

出典と根拠

ORDレコード
ord-c9c99943f4c4439aa5727f027386de43
出典データセット
uspto-grants-2010_04
特許番号
US07696223B2

関連ノート

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