Potassium Carbonate → 4-Chloro-6-methoxy-7-(2-methylthiazol-4-ylmethoxy)quinoline

Participants

Reaction Conditions

Reaction Steps

4-Chloromethyl-2-methylthiazole hydrochloride (226 mg, 1.23 mmol) was added to a suspension of 4-chloro-7-hydroxy-6-methoxyquinoline (216 mg, 1 mmol), (prepared as described for the starting material in Example 3), and potassium carbonate (483 mg, 3.5 mmol) in DMF (10 ml). The mixture was stirred for 2.5 hours at 70° C. The volatiles were removed by evaporation and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), the insoluble materials were removed by filtration and the volatiles were removed by evaporation. The residue was triturated with ether, collected by filtration, washed with ether and dried under vacuum to give 4-chloro-6-methoxy-7-(2-methylthiazol-4-ylmethoxy)quinoline (352 mg, 55%).

Provenance & Evidence