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

HRID 920925ノート

反応式

HRID 920925 の反応式
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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒HCID 21226129Dichloromethane methanol溶媒

反応条件

温度
130 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-394c0540575d491f9aafbadfe6484e0f
出典データセット
uspto-grants-2016_03
特許番号
US09273068B2

反応ノート

読み込み中…