Hydrochloric Acid → 5-(Pyridin-4-yl)-2-[2-(quinolin-2-yl)ethyl]phthalazin-1(2H)-one hydrochloride

HRID 920925노트

반응식

HRID 920925 반응식
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[N:5][N:6]([CH2:13][CH2:14][C:15]1[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=1)[C:7]2=[O:12].[N:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C([O-])([O-])=O.[Na+].[Na+].[ClH:40]>C(O)C.C1(C)C=CC=CC=1.CC(=O)OCC.C(Cl)Cl.CO>[ClH:40].[N:25]1[CH:30]=[CH:29][C:28]([C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[N:5][N:6]([CH2:13][CH2:14][C:15]2[CH:24]=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]=2)[C:7]3=[O:12])=[CH:27][CH:26]=1

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 866831355-Bromo-2-[2-(quinolin-2-yl)ethyl]phthalazin-1(2H)-one

생성물 1

HCID 866831375-(Pyridin-4-yl)-2-[2-(quinolin-2-yl)ethyl]phthalazin-1(2H)-one hydrochloride수율 72%

시약·촉매·용매 4

HCID 702Ethanol용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매HCID 21226129Dichloromethane methanol용매

반응 조건

온도
130 °C

실험 절차

A reaction tube was charged with a solution of 5-bromo-2-[2-(quinolin-2-yl)ethyl]phthalazin-1(2H)-one (70 mg, 0.184 mmol) in 1.5 mL of ethanol and 1.5 mL of toluene under argon. To this suspension, pyridin-4-ylboronic acid (22.63 mg, 0.184 mmol) and a 2M solution of Na2CO3 (39.2 mg, 0.369 mmol) were added. Then, tetrakis-(triphenylphoshine)palladium (21.27 mg, 0.018 mmol) was added. The reaction mixture was heated in a Biotage microwave at about 130° C. for about 30 min. The reaction was monitored by TLC (DCM/methanol=9:1). After completion of the reaction, EA was added followed by the addition of 1 N HCl. The mixture was extracted twice with EtOAc. The organic layer was basified with NaHCO3 and extracted with brine. The organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product was dissolved in isopropanol. Isopropanol containing HCl was added. The precipitate was sucked off and recrystallized from hot isopropanol to give a bright gray solid (55 mg, 72.0%).

후처리

  1. additionwas added
  2. extractionThe mixture was extracted twice with EtOAc
  3. extractionextracted with brine
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe crude product was dissolved in isopropanol
  8. additionIsopropanol containing HCl
  9. additionwas added
  10. customrecrystallized from hot isopropanol

출처 및 근거

ORD 기록
ord-394c0540575d491f9aafbadfe6484e0f
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273068B2

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