Methyl iodide → 1,5-Dimethyl-7-bromoindole

HRID 2215780

반응식

HRID 2215780 반응식
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]2[C:10](=[C:11]([Br:13])[CH:12]=1)[NH:9][CH:8]=[CH:7]2.[CH3:14]I>CN(C=O)C>[CH3:14][N:9]1[C:10]2[C:6](=[CH:5][C:4]([CH3:3])=[CH:12][C:11]=2[Br:13])[CH:7]=[CH:8]1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 34033307-Bromo-5-methyl-1H-indole

생성물 1

HCID 219499621,5-Dimethyl-7-bromoindole수율 96%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a suspension of sodium hydride (60%, 0.91 g, 22.9 mmol) in DMF (70 mL) was added a solution of 5-methyl-7-bromoindole (4.0 g, 19.05 mmol) in DMF (10 mL). The mixture was stirred at room temperature for 1 h, and then methyl iodide (1.78 mL, 28.6 mmol) was added with cooling in an ice-water-bath. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched with water and extracted with ethyl acetate. The extract was washed with water and brine, dried (sodium sulfate) and concentrated to give a crude product (4.1 g, 96%), which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 2.38 (s, 3H), 4.12 (s, 3H), 6.36 (d, J=3.12 Hz, 1H), 6.95 (d, J=3.13 Hz, 1H), 7.18 (d, J=1.56 Hz, 1H), 7.31 (dd, J1=0.79 Hz, J2=1.56 Hz, 1H).

후처리

  1. temperaturewith cooling in an ice-water-bath
  2. temperatureto warm to room temperature
  3. stirringstirred overnight
  4. customThe reaction was quenched with water
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water and brine
  7. dry with materialdried (sodium sulfate)
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-12bc21d35cd446ed8b153ecd0cccc676
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109229B2

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