Bromoacetonitrile → diethyl 1-(cyanomethyl)-1H-indole-2,6-dicarboxylate

HRID 1710447ノート

反応式

HRID 1710447 の反応式
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:11]=2)=[O:7])[CH3:4].Br[CH2:23][C:24]#[N:25]>CN(C=O)C>[CH2:3]([O:5][C:6]([C:8]1[N:9]([CH2:23][C:24]#[N:25])[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:11]=2)=[O:7])[CH3:4]

参加物

5

反応物 3

HCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 44754779Diethyl 1H-indole-2,6-dicarboxylate

生成物 1

HCID 58767564diethyl 1-(cyanomethyl)-1H-indole-2,6-dicarboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A mixture of 60% NaH in mineral oil (115 mg, 2.9 mmol) and 1H-indole-2,6-dicarboxylic acid diethyl ester (500 mg, 1.9 mmol) in DMF (3 mL) was stirred at room temperature for 0.5 h. Then bromo-acetonitrile in DMF (1 mL) was added and the reaction was warmed to 77° C. and kept at this temperature overnight. The reaction was cooled and quenched with ice water. A large amount of precipitate formed which was filtered and rinsed with water, followed by cold ether. The wet cake was dried in the vacuum oven (50° C.) to give 585 mg of 1-cyanomethyl-1H-indole-2,6-dicarboxylic acid diethyl ester.

後処理

  1. temperaturethe reaction was warmed to 77° C.
  2. customkept at this temperature overnight
  3. temperatureThe reaction was cooled
  4. customquenched with ice water
  5. customA large amount of precipitate formed which
  6. filtrationwas filtered
  7. washrinsed with water
  8. customThe wet cake was dried in the vacuum oven (50° C.)

出典と根拠

ORDレコード
ord-8a8bda555c114889991e7aa0b6747193
出典データセット
uspto-grants-2010_09
特許番号
US07790712B2

反応ノート

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