Sodium Hydroxide → HCID 178526791, 화합물

HRID 1943886노트

반응식

HRID 1943886 반응식
[OH-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]2[CH:14]=[N:13][NH:12][C:9]2=[N:10][CH:11]=1)([O-:5])=[O:4].[Br:15]Br>O1CCOCC1>[Br:15][C:14]1[C:8]2[C:9](=[N:10][CH:11]=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=2)[NH:12][N:13]=1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 123527765-nitro-1H-pyrazolo[3,4-b]pyridine

생성물 1

HCID 178526791HCID 178526791, 화합물수율 88.4%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

4N NaOH (5.12 mL, 20.5 mmol) was added to a cold (0° C.) solution of 5-nitro-1H-pyrazolo[3,4-b]pyridine (0.84 g, 5.12 mmol) in dioxane (30 mL), followed by bromine (1.05 mL, 20.5 mmol). The cold bath was removed, and the reaction mixture was left at room temperature for 30 minutes. The reaction mixture was diluted with ethyl acetate (100 mL) and quenched with saturated Na2S2O3 (50 mL) The aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layers were dried, filtered and concentrated. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (9:1) to give 3-bromo-5-nitro-1H-pyrazolo[3,4-b]pyridine (1.10 g, 88%) as a solid.

후처리

  1. customThe cold bath was removed
  2. additionThe reaction mixture was diluted with ethyl acetate (100 mL)
  3. customquenched with saturated Na2S2O3 (50 mL) The aqueous layer
  4. extractionwas extracted with ethyl acetate (100 mL)
  5. customThe combined organic layers were dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography
  9. washeluting with hexanes/ethyl acetate (9:1)

출처 및 근거

ORD 기록
ord-d257f01ec62249d69aa8daea52b29f83
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394795B2

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