反应详情

In a 10 mL round-bottomed flask, methyl 3-(bromomethyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylate (50 mg, 0.123 mmol) was combined with dichloromethane (5 mL) to give a colorless solution. Quinazolin-4-ylamine (17.8 mg, 0.123 mmol) and N,N-diisopropylethylamine (19.1 mg, 0.148 mmol) were added. The reaction mixture was stirred at room temperature overnight. TLC showed only starting material present after this time. Sodium hydride (60% suspension) (9.8 mg, 0.264 mmol) and 2 mL of THF were added. The reaction mixture was stirred at room temperature. The reaction mixture was poured into 25 mL H2O and extracted with ethyl acetate (1×25 mL). The organic layer was washed with 1 M HCl (1×10 mL), sat aqueous NaHCO3 (1×10 mL), and H2O (1×10 mL). The organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 4 g, 30% to 100% ethyl acetate in hexanes) to yield 7-chloro-4-oxo-1-phenyl-3-(quinazolin-4-ylaminomethyl)-1,4-dihydro-quinoline-2-carboxylic acid methyl ester. MS calcd. for C26H19ClN4O3 [(M+H)+] 471.1, obsd. 471.1.

1. customto give a colorless solution
2. stirringThe reaction mixture was stirred at room temperature
3. extractionextracted with ethyl acetate (1×25 mL)
4. washThe organic layer was washed with 1 M HCl (1×10 mL)
5. dry with materialThe organic layers were dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe crude material was purified by flash chromatography (silica gel, 4 g, 30% to 100% ethyl acetate in hexanes)