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Hydrochloric Acid → 3-(3-Methoxypyridin-4-yl)-5-[2-(quinolin-2-yl)ethyl]thieno[3,2-c]pyridin-4(5H)-one

HRID 920928
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 920928
Br[C:2]1[C:6]2[C:7](=[O:23])[N:8]([CH2:11][CH2:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.[CH3:24][O:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][C:31]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].Cl>C(O)C.C1(C)C=CC=CC=1.CC(=O)OCC.C(Cl)Cl.CO>[CH3:24][O:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][C:31]=1[C:2]1[C:6]2[C:7](=[O:23])[N:8]([CH2:11][CH2:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 467390193-Methoxypyridine-4-boronic acidHCID 866831403-bromo-5-[2-(quinolin-2-yl)ethyl]thieno[3,2-c]pyridin-4(5H)-on

Produkt 1

HCID 866831393-(3-Methoxypyridin-4-yl)-5-[2-(quinolin-2-yl)ethyl]thieno[3,2-c]pyridin-4(5H)-oneAusbeute 29,8 %

Reagenzien, Katalysatoren, Lösungsmittel

4
HCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 21226129Dichloromethane methanolLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A reaction tube was charged with a solution of 3-bromo-5-[2-(quinolin-2-yl)ethyl]thieno[3,2-c]pyridin-4(5H)-on (100 mg, 0.260 mmol) in 1.5 mL of ethanol and 1.5 mL of toluene under argon. To this suspension, 3-methoxypyridin-4-ylboronic acid (39.7 mg, 0.260 mmol) and a 2M solution of Na2CO3 (41.3 mg, 0.389 mmol) were added. Then, tetrakis(triphenylphoshine)palladium (30.0 mg, 0.026 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 ethyl acetate to give a white solid (32 mg, 29.8%).

Aufarbeitung

  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 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ab9ad1bc43a842d1addd2c5e0d0d7d05
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09273068B2

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