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

HRID 642416

반응식

HRID 642416 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c9c99943f4c4439aa5727f027386de43
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696223B2

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