Cesium carbonate → 854514-88-8

Participants

Reaction Steps

A solution of 4-(2-chloroethyl)morpholine (2.1 g, 11.5 mmol) and Cs2CO3 (7.5 g, 23 mmol) in CH3CN (100 mL) was stirred for 45 minutes at room temperature. To the solution was added 6-[(7-hydroxyquinolin-4-yl)oxy]-N,2-dimethyl-1-benzofuran-3-carboxamide (2 g, 5.75 mmol). The mixture was heated to reflux for 3 hrs. Inorganic salt was removed by filtration and the solution was concentrated. The residue was purified by a silica gel column chromatography (using 1 to 10% MeOH/CH2Cl2) to give 1.8 g of free base N,2-dimethyl-6-[7-(2-morpholinoethoxy)quinolin-4-yloxy]benzofuran-3-carboxamide as a solid. The compound was then dissolved in hot isopropanol and stirred at room temperature overnight. 1.13 g of N,2-dimethyl-6-[7-(2-morpholinoethoxy)quinolin-4-yloxy]benzofuran-3-carboxamide as polymorph Form 2 was collected by filtration. Note, Form 2 is anhydrous and must be prepared under water-free conditions in order to prevent hydrate formation (such as Form 4 as described in Example 6).

Provenance & Evidence