Benzoic Acid → (cis)-Naphthalen-2-ylmethyl 3-(benzoyloxy)-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)piperidine-1-carboxylate

Participants

Reaction Steps

(trans)-Naphthalen-2-ylmethyl 3-hydroxy-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)piperidine-1-carboxylate (Example 28, Steps A-D; 0.075 g, 0.121 mmol) was dissolved in THF (0.50 mL) and treated with benzoic acid (0.022 g, 0.181 mmol), PPh3 (0.036 g, 0.139 mmol) and diisopropylazodicarboxylate (0.026 ml, 0.133 mmol). The mixture was stirred at ambient temperature for 40 hours, and then the whole reaction mixture was applied to a column of SiO2 and eluted with a gradient from 1-20% (6% NH4OH in MeOH)/ethyl acetate (75 mg). MS ESI (+) m/z 723.2 (M+1) detected.

Provenance & Evidence