Tetrahydrofuran → HCID 66936733, Verbindung

HRID 1943740Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1943740
O1CCCC1.Br[C:7]1[CH:16]=[N:15][C:10]2[O:11][CH2:12][CH2:13][NH:14][C:9]=2[CH:8]=1.CC1(C)C(C)(C)OB([C:25]2[CH:33]=[CH:32][CH:31]=[C:30]3[C:26]=2[CH:27]=[CH:28][NH:29]3)O1.C(=O)([O-])[O-].[K+].[K+]>O>[NH:29]1[C:30]2[C:26](=[C:25]([C:7]3[CH:16]=[N:15][C:10]4[O:11][CH2:12][CH2:13][NH:14][C:9]=4[CH:8]=3)[CH:33]=[CH:32][CH:31]=2)[CH:27]=[CH:28]1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 113224711H-Indole-4-boronic acid, pinacol esterHCID 667890617-bromo-1H,2H,3H-pyrido[2,3-b][1,4]oxazine

Produkt 1

HCID 66936733HCID 66936733, VerbindungAusbeute 139,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To 3 ml of tetrahydrofuran (THF)/0.5 ml of distilled water, 7-bromo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine (80.0 mg, 0.37 mmol), 4-(4,4,5,5,-tetramethyl-[1,3,2]dioxaborolane-2-yl)-1H-indole (109 mg, 0.45 mmol), potassium carbonate (103 mg, 0.74 mmol) and tetrakis triphenylphosphine palladium (172 mg, 0.15 mmol) were added and stirred at 80° C. for 4 hours. After completion of the reaction, the mixture was extracted with ethyl acetate, and the combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on amine silica eluting with a solvent of dichloromethane:methanol=40:1. The fractions containing the product were collected and evaporated to obtain 7-(1H-indol-4-yl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine as white solid (130 mg).

Aufarbeitung

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on amine silica eluting with a solvent of dichloromethane
  7. additionThe fractions containing the product
  8. customwere collected
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-05a591a6f3ba4285915111af68f57a83
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394792B2

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