Methanol → 2-Chloro-8-fluoroindolo[2,1-b]quinazoline-6,12-dione

HRID 215794

Reaktionsgleichung

Reaktionsgleichung von HRID 215794
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=O)[C:7]2=[O:14].[Cl:15][C:16]1[CH:27]=[C:20]2[C:21](OC(=O)[NH:25][C:19]2=[CH:18][CH:17]=1)=[O:22].CO>CN(C=O)C.C(Cl)(Cl)Cl>[Cl:15][C:16]1[CH:27]=[C:20]2[C:19](=[CH:18][CH:17]=1)[N:25]=[C:8]1[C:7](=[O:14])[C:6]3[C:10]([N:9]1[C:21]2=[O:22])=[CH:11][CH:12]=[C:4]([F:3])[CH:5]=3

Komponenten

7

Edukt 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 784805-Chloroisatoic anhydrideHCID 2365665-Fluoroisatin

Produkt 1

HCID 4785692-Chloro-8-fluoroindolo[2,1-b]quinazoline-6,12-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

To a suspension of NaH (10 mmol, 40 mg 60%) in 4 mL of DMF was added 10 mmol of 5-fluoroisatin in 2 mL of DMF. After 15 min, a solution of 5-chloroisatoic anhydride in 3 mL of DMF was added. The reaction mixture was stirred for 18 h, methanol (0.5 mL) and 20 mL of chloroform was added and the organic solution was washed with water, dried (MgSO4) and concentrated to give a residue that was purified by silica gel chromatography (CHCl3:CH3OH). Yield 77%: mp 280-282° C.

Aufarbeitung

  1. washthe organic solution was washed with water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customto give a residue that
  5. customwas purified by silica gel chromatography (CHCl3:CH3OH)

Quellen und Nachweise

ORD-Eintrag
ord-fd13265b4c7b46ac9ab24a8ebf6c8904
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193185B2

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