A 100 mL round-bottomed flask was charged with 1-((4-fluorophenyl)carbamoyl)cyclopropane carboxylic acid (0.3516 g, 0.9767 mmol; prepared from cyclopropane-1,1-dicarboxylic acid and 4-fluoroaniline in THF (25 mL) using the methods of WO 2005/030140 and Shih and Rankin, Synth. Comm., 1996, 26(4), 833-836). Next, catalytic DMF (10 microliters) was added. While stirring oxalyl dichloride (0.08387 mL, 0.9767 mmol) was added. The reaction mixture was stirred for 30 minutes and 4-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)benzenamine (0.160 g, 0.3907 mmol) in THF (2 mL) was added. The reaction mixture was stirred for 1 hour, the diluted with water (50 mL) and saturated NaHCO3 (50 mL). The reaction mixture was extracted with EtOAc, washed with brine, dried organic over sodium sulfate, filtered and concentrated. The reaction mixture was purified by preparative TLC (0.5 mm) eluting with EtOAc. The product (90 mg, 28%) was obtained as a white solid. LRMS (esi pos) m/e 566 (M+1).
