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

HRID 2360488ノート

反応式

HRID 2360488 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒2 回HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8a97a9a8ac2e4c72bfde979aa9bcad87
出典データセット
uspto-grants-2014_04
特許番号
US08686022B2

反応ノート

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