Acetic Acid → 5-Bromo-3-(2-chloro-4-cyanobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine

HRID 1072915ノート

反応式

HRID 1072915 の反応式
[Br:1][C:2]1[N:7]=[C:6]([N:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][C:14]=2[Cl:21])[C:9](=O)[CH3:10])[C:5]([N+:22]([O-])=O)=[CH:4][CH:3]=1.C(O)(=O)C>C(O)C.[Fe]>[Br:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][C:14]=3[Cl:21])[C:9]([CH3:10])=[N:22][C:5]2=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 176Acetic AcidHCID 223878586-Bromo-2-(N-(2-chloro-4-cyanobenzyl)acetamido)-3-nitropyridine

生成物 1

HCID 223879675-Bromo-3-(2-chloro-4-cyanobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine収率 9.9%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

実験手順

To a solution of 6-bromo-2-(N-(2-chloro-4-cyanobenzyl)acetamido)-3-nitropyridine (21.8 g) in ethanol (33 ml)-acetic acid (8.3 ml) was added iron powder (2.29 g) at room temperature, and the mixture was refluxed under heating for 2 hr. The reaction mixture was cooled, the insoluble matter was removed by filtration, and the solvent was evaporated. To the residue was added dichloromethane, and the product was extracted. The solvent was evaporated and the residue was purified by silica gel column chromatography (dichloromethane/methanol=30/1) to give the objective compound (1.90 g) as a pale-yellow powder.

後処理

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 2 hr
  3. temperatureThe reaction mixture was cooled
  4. customthe insoluble matter was removed by filtration
  5. customthe solvent was evaporated
  6. additionTo the residue was added dichloromethane
  7. extractionthe product was extracted
  8. customThe solvent was evaporated
  9. customthe residue was purified by silica gel column chromatography (dichloromethane/methanol=30/1)

出典と根拠

ORDレコード
ord-0c648d40af0847e4ba22298d9f00b680
出典データセット
uspto-grants-2005_06
特許番号
US06911469B2

反応ノート

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