Acetonitrile → HCID 11281937, compound

Participants

Reaction Steps

A solution of 6-[(7-hydroxyquinolin-4-yl)oxy]-N,2-dimethyl-1-benzofuran-3-carboxamide 119-A (200mg, 0.57 mmol), methyl 4-bromobutanoate (155mg, 0.85 mmol), and Cs2CO3 (433 mg, 1.14 mmol) in a mixed solvent of CH3CN (4 mL)/DMF(1 mL) was heated to 65° C. overnight. The reaction mixture was extracted with EtOAc, concentrated and dissolved in 5 mL of MeOH. To the solution was added 1 N NaOH (1 mL). The solution was stirred at room temperature for 2 hours and then heated to 60° C. for 2 hours. The solution was acidified with AcOH to a pH of about 6 and extracted with EtOAc. The concentrated residue was purified by HPLC using 20-60% CH3CN/H2O over 30 min. to give 4-{[4-({2-methyl-3-[(methylamino)carbonyl]-1-benzofuran-6-yl}oxy)quinolin-7-yl]oxy}butanoic acid 119.

Provenance & Evidence