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

HRID 1072915노트

반응식

HRID 1072915 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0c648d40af0847e4ba22298d9f00b680
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06911469B2

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