Hydrochloric Acid → 1-(2,3-Dihydro-[1,4]dioxino[2,3-b]pyridin-7-yl)ethan-1-one

HRID 1038584Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1038584
Br[C:2]1[CH:3]=[C:4]2[O:11][CH2:10][CH2:9][O:8][C:5]2=[N:6][CH:7]=1.[CH2:12]([O:14]C([Sn](CCCC)(CCCC)CCCC)=C)[CH3:13].Cl>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:11]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:12](=[O:14])[CH3:13])[CH:3]=2)[O:8][CH2:9][CH2:10]1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 133540297-bromo-2H,3H-[1,4]dioxino[2,3-b]pyridine

Produkt 1

HCID 665985031-(2,3-Dihydro-[1,4]dioxino[2,3-b]pyridin-7-yl)ethan-1-oneAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Under an argon atmosphere, 7-bromo-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine (65 mg, 0.30 mmol) was dissolved in toluene (1.5 mL), added tetrakis(triphenylphosphine)palladium (35 mg, 0.03 mmol) and 1-ethoxyethenyl tri n-butyl tin (112 ΞL, 0.33 mmol), and the mixture was stirred at 100° C. overnight. The reaction solution was reverted to room temperature, and added 1N hydrochloric acid. The reaction solution was filtered through a pad of celite. The reaction solution was added ethyl acetate for extraction. The organic layer was washed with brine, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by preparative thin-layer chromatography (n-hexane/ethyl acetate=1/1). The title compound (37 mg (yield 69%)) was obtained as a white solid.

Aufarbeitung

  1. customwas reverted to room temperature
  2. filtrationThe reaction solution was filtered through a pad of celite
  3. additionThe reaction solution was added ethyl acetate
  4. extractionfor extraction
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. custompurified by preparative thin-layer chromatography (n-hexane/ethyl acetate=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-4bf9fc92f3c143c6a96324bd6b516291
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08551985B2

Notizen zur Reaktion

Wird geladen…