Phosphorus oxybromide → ethyl 6-bromo-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

HRID 1909163ノート

反応式

HRID 1909163 の反応式
O[C:2]1[CH:3]=[C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5]2[CH:10]=[N:9][NH:8][C:6]=2[N:7]=1.P(Br)(Br)([Br:18])=O>C(#N)C>[Br:18][C:2]1[CH:3]=[C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5]2[CH:10]=[N:9][NH:8][C:6]=2[N:7]=1

参加物

4

反応物 2

HCID 24613Phosphorus oxybromideHCID 178469358ethyl 6-oxo-1,2-dihydropyrazolo[3,4-b]pyridine-4-carboxylate

生成物 1

HCID 59766670ethyl 6-bromo-1H-pyrazolo[3,4-b]pyridine-4-carboxylate収率 77.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

Ethyl 6-hydroxy-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (25 g, 120 mmol) was suspended in acetonitrile (250 mL) and POBr3 (69.56 g, 241.54 mmol) was added to it. The reaction mixture was refluxed for 6 h. On completion of reaction, acetonitrile was removed under reduced pressure and residue neutralized with saturated NaHCO3 solution was added to it. Extraction was carried out using ethyl acetate; the combined organic layers were washed with water, brine and dried over anhydrous Na2SO4; filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to provide the desired intermediate (25 g, 77%).

後処理

  1. temperatureThe reaction mixture was refluxed for 6 h
  2. customwas removed under reduced pressure and residue
  3. additionwas added to it
  4. extractionExtraction
  5. washthe combined organic layers were washed with water, brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-1cb4bca67bfb4cbeba133987e6cf70d4
出典データセット
uspto-grants-2013_12
特許番号
US08598167B1

反応ノート

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