Cesium carbonate → 854514-88-8

Participants

Reaction Conditions

Reaction Steps

A solution of 4-(2-chloroethyl)morpholine (10.7 g, 57.4 mmol) and Cs2CO3 (46.3 g, 143.5 mmol) in DMF (100 mL) was stirred for 1 hour at room temperature. To the solution was added a solution of 6-[(7-hydroxyquinolin-4-yl)oxy]-N,2-dimethyl-1-benzofuran-3-carboxamide (10 g, 28.7 mmol). The mixture was heated to 120° C. for 15 hr. The solution was cooled to room temperature and extracted with EtOAc. The concentrated residue was purified by a silica gel column chromatography (using 5 to 10%) MeOH/CH2Cl2) to give 2.6 g of free base N,2-dimethyl-6-[7-(2-morpholinoethoxy)quinolin-4-yloxy]benzofuran-3-carboxamide as a solid. The solid free base was identified as Form 1 as characterized by powder X-ray diffraction as shown in FIG. 11. Note, Form 1 can also be prepared by slurrying any of Forms 3, 5, or 6 in water at room temperature for 24 hours.

Provenance & Evidence