A solution of 7-azaoxindole (165 mg, 1.23 mmol), (prepared as described for the starting material in Example 2), in DMF (3 ml) was added dropwise to a suspension of sodium hydride (50 mg, 1.23 mmol, prewashed with hexane) in DMF (3 ml). After stirring for 30 minutes at ambient temperature, 4-chloro-7-(2-(imidazol-1-yl)ethoxy)-6-methoxyquinazoline (125 mg, 0.41 mmol) in DMF (3 ml) was added. The mixture was heated at 65° C. for 30 minutes. After cooling the mixture was partitioned between saturated aqueous ammonium chloride and methylene chloride. The precipitate was collected by filtration, dried and purified by flash chromatography eluting with methylene chloride/methanol (8/2). After evaporation of the solvent, the solid was dissolved in methylene chloride/methanol and 2.2 M hydrogen chloride in ether was added. After stirring for 10 minutes at ambient temperature, the volatiles were removed by evaporation. The residue was triturated with ether, collected by filtration and dried under vacuum to give 4-(7-azaoxindol-3-yl)-7-(2-(imidazol-1-yl)ethoxy)-6-methoxyquinazoline (110 mg, 53%).
