Hydroxyamine hydrochloride → 5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

HRID 2088966노트

반응식

HRID 2088966 반응식
Cl.[NH2:2]O.[Br:4][C:5]1[CH:6]=[C:7]2[C:13]([CH:14]=O)=[CH:12][NH:11][C:8]2=[N:9][CH:10]=1.C(=O)(O)[O-].[Na+]>CO>[Br:4][C:5]1[CH:6]=[C:7]2[C:13]([C:14]#[N:2])=[CH:12][NH:11][C:8]2=[N:9][CH:10]=1

참가 물질

5

반응물 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 247296055-bromo-1H-pyrrolo(2,3-b)pyridine-3-carbaldehyde

생성물 1

HCID 280587935-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Hydroxylamine hydrochloride (46 mg) was added to a suspension of 5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde obtained by the method of described in WO 2004/101565 (150 mg) in methanol (1.0 ml) under nitrogen atmosphere, and the mixture was stirred at room temperature for one hour. After azeotropic distillation with toluene, thionyl chloride (118 μl) was added to a suspension of the residue in toluene (2 ml), and the mixture was stirred at 80° C. for 16 hours and at 100° C. for 8 hours. After leaving to cool to room temperature, saturated aqueous sodium bicarbonate was added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developed with methanol-chloroform) to give the title compound (88 mg).

후처리

  1. customobtained by the method
  2. distillationAfter azeotropic distillation with toluene, thionyl chloride (118 μl)
  3. additionwas added to a suspension of the residue in toluene (2 ml)
  4. stirringthe mixture was stirred at 80° C. for 16 hours and at 100° C. for 8 hours
  5. customAfter leaving
  6. temperatureto cool to room temperature
  7. extractionfollowed by extraction with ethyl acetate
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customThe resulting residue was purified by silica gel column chromatography (developed with methanol-chloroform)

출처 및 근거

ORD 기록
ord-1e333bb1a62a4d04967600331383b3cf
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436012B2

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