5-Azaindole → 2-(2-Fluoro-phenyl)-4-pyrrolo[3,2-c]pyridin-1-yl-quinazoline

HRID 457713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 457713
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[N:3]=1.[NH:19]1[C:27]2[CH:26]=[CH:25][N:24]=[CH:23][C:22]=2[CH:21]=[CH:20]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:4]1[N:3]=[C:2]([N:19]2[C:27]3[CH:26]=[CH:25][N:24]=[CH:23][C:22]=3[CH:21]=[CH:20]2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Komponenten

5

Edukt 3

HCID 92205-AzaindoleHCID 10796Cesium carbonateHCID 47382154-Chloro-2-(2-fluoro-phenyl)-quinazoline

Produkt 1

HCID 184406432-(2-Fluoro-phenyl)-4-pyrrolo[3,2-c]pyridin-1-yl-quinazoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

4-Chloro-2-(2-fluoro-phenyl)-quinazoline from Step C (0.1 g, 0.38 mmol) was dissolved in N,N-dimethylformamide (1 ml) and to it was added 1H-pyrrolo[3,2-c]pyridine (0.046 g, 0.38 mmol) followed by cesium carbonate (0.134 g, 0.41 mmol). The mixture was magnetically stirred and heated to 100° C. for 0.5 hr. The solvent was removed and title compound was obtained pure after column purification on a HPLC reverse phase column, using a water and acetonitrile gradient containing 0.1% trifluoroacetic acid to yield (0.072 g, 56%). MS (ES) 340.1 (M+H)+

Aufarbeitung

  1. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-afe77a0d3a3b4559a2c78cbf69e04e6f
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07189733B2

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