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

HRID 920940노트

반응식

HRID 920940 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 702Ethanol용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
130 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-ac5cf906be00415f981a05b026a024ad
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273068B2

반응 노트

불러오는 중…