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Cesium carbonate → 6-(4-hydroxy-phenyl)-3-((E)-styryl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 82035
ノート
印刷プレビュー

反応式

HRID 82035 の反応式
C([O:3][C:4]([C:6]1[C:7]2[C:15](/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:14][N:13]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)[C:8]=2[N:9]=[C:10](Cl)[CH:11]=1)=[O:5])C.[OH:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:30][C:31]1[CH:36]=[CH:35][C:34]([C:10]2[CH:11]=[C:6]([C:4]([OH:3])=[O:5])[C:7]3[C:15](/[CH:16]=[CH:17]/[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)=[N:14][N:13]([CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][O:25]4)[C:8]=3[N:9]=2)=[CH:33][CH:32]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 27343604-Hydroxyphenylboronic acidHCID 866781696-chloro-3-((E)-styryl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester

生成物 1

HCID 1363594996-(4-hydroxy-phenyl)-3-((E)-styryl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid収率 79%

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 6-chloro-3-((E)-styryl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester (2.8 g, 6.80 mmol) in dioxane (60 ml) were added 4-hydroxyphenylboronic acid (1.03 g, 7.48 mmol) and an aqueous solution of cesium carbonate (0.4M, 30 mL). The resulting solution was degassed using argon, tetrakis(triphenylphosphine)palladium (0.71 g, 0.61 mmol) was then added and the reaction mixture was refluxed overnight. Dioxane was removed under vacuum, methylene chloride and water were added, and the mixture was acidified until pH=2. The organic layer was washed with water and the aqueous phase was extracted using methylene chloride. The resulting organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (2.37 g, 79%) as a yellow solid which was used without any further purification.

後処理

  1. customThe resulting solution was degassed
  2. additionwas then added
  3. temperaturethe reaction mixture was refluxed overnight
  4. customDioxane was removed under vacuum, methylene chloride and water
  5. additionwere added
  6. washThe organic layer was washed with water
  7. extractionthe aqueous phase was extracted
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-f981aef52ac943de9e3a06645bd07ce1
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08846712B2

反応ノート

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