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

HRID 82039

反応式

HRID 82039 の反応式
C([O:3][C:4]([C:6]1[C:7]2[C:15]([CH:16]=[CH2:17])=[N:14][N:13]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][O:19]3)[C:8]=2[N:9]=[C:10](Cl)[CH:11]=1)=[O:5])C.[OH:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=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:24][C:25]1[CH:30]=[CH:29][C:28]([C:10]2[CH:11]=[C:6]([C:4]([OH:3])=[O:5])[C:7]3[C:15]([CH:16]=[CH2:17])=[N:14][N:13]([CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][O:19]4)[C:8]=3[N:9]=2)=[CH:27][CH:26]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 27343604-Hydroxyphenylboronic acidHCID 866781686-chloro-1-(tetrahydro-pyran-2-yl)-3-vinyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester

生成物 1

HCID 1363595036-(4-hydroxy-phenyl)-1-(tetrahydro-pyran-2-yl)-3-vinyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid収率 143.7%

試薬・触媒・溶媒 2

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

実験手順

To a solution of 6-chloro-1-(tetrahydro-pyran-2-yl)-3-vinyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester (2.00 g, 5.96 mmol), described in example 16.1, in dioxane (54 mL) were added 4-hydroxyphenylboronic acid (0.90 g, 6.55 mmol) and an aqueous solution of cesium carbonate (0.4 M, 27 mL, 10.8 mmol). The resulting solution was degassed using argon, tetrakis(triphenylphosphine)palladium (0.62 g, 0.54 mmol) was then added and the reaction mixture was refluxed overnight. Dioxane was removed under vacuum, water was added and then the mixture was acidified to pH=2. The aqueous phase was extracted with a mixture of tetrahydrofuran and EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered, concentrated under vacuum to give the title compound (3.13 g) as a brown foam which was used without 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, water
  5. additionwas added
  6. extractionThe aqueous phase was extracted with a mixture of tetrahydrofuran and EtOAc
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-8d689576def44b3cae178a21b4357d6c
出典データセット
uspto-grants-2014_09
特許番号
US08846712B2

関連ノート

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