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

HRID 920941Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 920941
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[N:34]1[CH:39]=[CH:38][C:37]([C:40]2[C:44]3[C:45](=[O:49])[NH:46][CH:47]=[CH:48][C:43]=3[O:42][CH:41]=2)=[CH:36][CH:35]=1.[N:50]1[C:59]2[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=2)[CH:53]=[CH:52][C:51]=1[CH2:60][CH2:61]O.Cl>C1COCC1.CC(=O)OCC>[N:34]1[CH:35]=[CH:36][C:37]([C:40]2[C:44]3[C:45](=[O:49])[N:46]([CH2:61][CH2:60][C:51]4[CH:52]=[CH:53][C:54]5[C:59](=[CH:58][CH:57]=[CH:56][CH:55]=5)[N:50]=4)[CH:47]=[CH:48][C:43]=3[O:42][CH:41]=2)=[CH:38][CH:39]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 705322-QuinolineethanolHCID 5363146Diisopropyl azodicarboxylateHCID 866831543-(Pyridin-4-yl)furo[3,2-c]pyridin-4(5H)-one

Produkt 1

HCID 866831553-(Pyridin-4-yl)-5-(2-(quinolin-2-yl)ethyl)furo[3,2-c]pyridin-4(5H)-oneAusbeute 36,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
15 °C

Versuchsvorschrift

To a solution of triphenylphosphine (247 mg, 0.942 mmol) in THF (10 mL), DIAD (0.321 mL, 1.65 mmol) was added. The mixture was cooled to 15° C. 3-(Pyridin-4-yl)furo[3,2-c]pyridin-4(5H)-one (100 mg, 0.471 mmol) and 2-(quinolin-2-yl)ethanol from example from example a1 were added. After stirring overnight at room temperature, EA and 2M HCl were added. The phases were separated and extracted with EA. The organic phase was washed with water. The acidic aqueous phase was basified with 2M NaOH and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography to give 69 mg of the title compound (36.3%) as hydrochloride salt as dark yellow solid.

Aufarbeitung

  1. customThe phases were separated
  2. extractionextracted with EA
  3. washThe organic phase was washed with water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4d092cf5421746948d7091afacfa9724
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273068B2

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