Potassium Carbonate → 5-{[2-(4-Fluoro-phenyl)-5-iodo-3-methylcarbamoyl-furo[2,3-b]pyridin-6-yl]-methanesulfonyl-amino}-pentanoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To 2-(4-Fluoro-phenyl)-5-iodo-6-methanesulfonylamino-furo[2,3-b]pyridine-3-carboxylic acid methylamide (300 mg, 0.613 mmol), K2CO3 (169 mg, 1.226 mmol), KI (1018 mg, 6.13 mmol), and methyl 5-bromopentanoate (250 μl, 1.747 mmol) is added acetone (3066 μl) and the reaction mixture is stirred at 60° C. overnight. The acetone is removed under N2 and the mixture is taken up in 2 mL 1:1:1 DMF/H2O/ACN and filtered with a 0.45μ PTFE filter. Purification is achieved by reverse phase HPLC with a C8 column with 40-80% MeOH (0.1% TFA)/H2O (0.1% TFA). MS (ESI) m/z 604.0 (M+1). Retention time=1.48 min, Method A. 1H NMR (400 MHz, CDCl3 d ppm 8.77 (s, 1H), 7.96 (t, 2H), 7.19-7.36 (m, 2H), 5.80 (br s, 1H), 3.68 (t, 2H), 3.54 (s, 3H), 3.14 (s, 3H), 2.97 (d, 3H), 2.29 (t, 2H), 1.69-1.79 (m, 2H), 1.42 (s, 2H)

Provenance & Evidence