Tetrahydrofuran → HCID 67416078, Verbindung

HRID 2192992Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2192992
Cl[C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:5]=1[C:6](Cl)=[N:7]2.C(OC([N:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27](B(O)O)=[CH:26]1)=O)(C)(C)C.C1C[O:40]CC1>C([O-])([O-])=O.[Na+].[Na+]>[F:17][C:15]1[CH:14]=[CH:13][C:5]2[C:6]([C:27]3[C:28]4[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=4)[NH:25][CH:26]=3)=[N:7][C:8]3[CH:9]=[CH:10][NH:11][C:2](=[O:40])[C:3]=3[C:4]=2[CH:16]=1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 52330101-(tert-Butoxycarbonyl)indole-3-boronic acidHCID 59375375HCID 59375375, Verbindung

Produkt 1

HCID 67416078HCID 67416078, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10340Sodium CarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a solution of 1,6-dichloro-9-fluorobenzo[c]-1,6-naphthyridine (20 mg, 0.075 mmol) in THF (2 mL) and 2.0 M Na2CO3 (500 μL) were added [1-(tert-butoxycarbonyl)-1H-indol-3-yl]boronic acid (23.5 mg, 0.09 mmol). The solution was degassed by bubbling N2 for 5 min heated to 150° C. for 1 hr in a microwave reactor. The reaction solution was extracted with EtOAc and water, the organic layers were dried with MgSO4, filtered, and concentrated by rotary evaporation. Silcia gel column chromatography with 100% CH2Cl2 to 25% MeOH provided the 9-fluoro-6-(1H-indol-3-yl)benzo[c]-1,6-naphthyridin-1(2H)-one. LRMS (ESI) calc'd for (C20H13FN3O) [M+H]+, 330.1; found 330.1

Aufarbeitung

  1. customThe solution was degassed
  2. customby bubbling N2 for 5 min
  3. extractionThe reaction solution was extracted with EtOAc and water
  4. dry with materialthe organic layers were dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-a9fb2cca65cf4a3691ae162e141238ab
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329722B2

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