Hydrochloric Acid → 3-(Pyridin-4-yl)furo[3,2-c]pyridin-4(5H)-one

HRID 920940ノート

反応式

HRID 920940 の反応式
Br[C:2]1[C:6]2[C:7](=[O:11])[NH:8][CH:9]=[CH:10][C:5]=2[O:4][CH:3]=1.[N:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+].Cl>CC(=O)OCC.C1(C)C=CC=CC=1.C(O)C>[N:12]1[CH:17]=[CH:16][C:15]([C:2]2[C:6]3[C:7](=[O:11])[NH:8][CH:9]=[CH:10][C:5]=3[O:4][CH:3]=2)=[CH:14][CH:13]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 108462753-bromofuro[3,2-c]pyridin-4(5H)-one

生成物 1

HCID 866831543-(Pyridin-4-yl)furo[3,2-c]pyridin-4(5H)-one収率 43.4%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
130 °C

実験手順

A reaction tube was charged with 3-bromofuro[3,2-c]pyridin-4(5H)-one (1000 mg, 4.67 mmol) and a mixture of 1 mL of ethanol and 1 mL of toluene under argon. To this mixture, pyridin-4-ylboronic acid (574 mg, 4.67 mmol) and a 2 M solution of Na2CO3 (743 mg, 7.01 mmol) were added followed by the addition of tetrakis-(triphenylphoshine)palladium (540 mg, 0.467 mmol). The reaction mixture was heated in a Cem microwave at about 130° C. for about 30 min. After completion of the reaction, EA was added followed by the addition of 2 N HCl. The mixture was extracted twice with EtOAc. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product was purified by chromatography to give the title compound as dark yellow solid (430 mg, 43.4%).

後処理

  1. additionwas added
  2. extractionThe mixture was extracted twice with EtOAc
  3. extractionThe aqueous layer was extracted three times with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by chromatography

出典と根拠

ORDレコード
ord-ac5cf906be00415f981a05b026a024ad
出典データセット
uspto-grants-2016_03
特許番号
US09273068B2

反応ノート

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