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Hydrochloric Acid → Quinoxalin-6-ylboronic acid

HRID 571447
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 571447
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([B:11]3[O:19]C(C)(C)C(C)(C)[O:12]3)=[CH:8][CH:9]=2)[N:4]=[CH:3][CH:2]=1.O.Cl.CCOC(C)=O>C1COCC1>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([B:11]([OH:19])[OH:12])=[CH:8][CH:9]=2)[N:4]=[CH:3][CH:2]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 441182986-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline

Produkt 1

HCID 45073596Quinoxalin-6-ylboronic acidAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

To 6-quinoxaline boronic acid pinacol ester (S50) (256 mg, 1.00 mmol, 1.00 equiv) in THF (2.0 mL) at 23° C. was added H2O (8.0 mL) and NaIO4 (321 mg, 1.50 mmol, 1.50 equiv). After stirring for 1.0 hr at 23° C., the reaction mixture was added to 1N HCl aq (20 mL) and was further stirred for 1.0 hr. To the reaction mixture was added EtOAc (20 mL) and the phases were separated. The aqueous phase was extracted with EtOAc (2×20 mL). The combined organic phases are washed with brine (20 mL) and dried (Na2SO4). The filtrate was concentrated in vacuo and the residue was triturated with Et2O to afford 121 mg of the title compound as a colorless solid (70% yield).

Aufarbeitung

  1. stirringwas further stirred for 1.0 hr
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted with EtOAc (2×20 mL)
  4. washThe combined organic phases are washed with brine (20 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was triturated with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-f8c6885228864c989c953c677f519d3e
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09024093B2

Notizen zur Reaktion

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