Sodium Hydroxide → HCID 178526791、化合物

HRID 1943886ノート

反応式

HRID 1943886 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 178526791HCID 178526791、化合物収率 88.4%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d257f01ec62249d69aa8daea52b29f83
出典データセット
uspto-grants-2013_03
特許番号
US08394795B2

反応ノート

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