Methyl iodide → 7-bromo-1-methyl-1H-indole-2-carboxylic acid

HRID 2360488

반응식

HRID 2360488 반응식
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13]CC)=[O:12])=[CH:7]2.[H-].[Na+].[CH3:18]I.[OH-].[Na+]>CN(C)C=O.O.CO>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH3:18])[C:8]([C:11]([OH:13])=[O:12])=[CH:7]2

참가 물질

8

반응물 4

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 7017885Ethyl 7-bromo-1H-indole-2-carboxylate

생성물 1

HCID 584939967-bromo-1-methyl-1H-indole-2-carboxylic acid

시약·촉매·용매 3

HCID 887Methanol용매2회HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

7.37 g ethyl 7-bromo-1H-indole-2-carboxylate are dissolved in 50 ml N,N-dimethylformamide, cooled to 0° C. and combined with 1.16 g sodium hydride (60% in mineral oil). The mixture is stirred for 20 minutes and then 1.78 ml methyl iodide are added dropwise. Then the mixture is allowed to come up to ambient temperature and stirred for 12 hours. Then 80 ml of methanol and 27.5 ml 2 N sodium hydroxide solution are added and the mixture is stirred for 3 hours at ambient temperature. The methanol is eliminated in vacuo, the residue is mixed with water and the precipitate is suction filtered. The filtrate is washed twice with ethyl acetate and the aqueous phase is combined with sufficient 2 N hydrochloric acid to give a pH of 2. The precipitated solid is suction filtered, washed with water and dried.

후처리

  1. customto come up to ambient temperature
  2. stirringstirred for 12 hours
  3. stirringthe mixture is stirred for 3 hours at ambient temperature
  4. filtrationfiltered
  5. washThe filtrate is washed twice with ethyl acetate
  6. customto give a pH of 2
  7. filtrationfiltered
  8. washwashed with water
  9. customdried

출처 및 근거

ORD 기록
ord-8a97a9a8ac2e4c72bfde979aa9bcad87
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08686022B2

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