Water → (3R,4R)-naphthalen-2-ylmethyl 3-fluoro-4-(6-fluoro-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

(3R,4S)-naphthalen-2-ylmethyl 3-fluoro-4-(methylsulfonyloxy)piperidine-1-carboxylate (170 mg, 0.44 mmol) (Example 20, Step F, derived from Peak 2), 6-fluoro-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-ol (173 mg, 0.49 mmol) and Cs2CO3 (290 mg, 0.89 mmol) were weighed into a flask and suspended in 10 mL of DMA. The reaction was then heated to 90° C. overnight. The reaction was then cooled to ambient temperature, followed by workup with water and EtOAc. The combined organic phase was concentrated in vacuo, followed by flash column chromatography (1-10% MeOH/DCM) affording the desired product as a brown semi-solid (270 mg, 0.43 mmol, 95%). MS APCI (+) m/z 639.2 and 640.1 (M+1/+3) detected.

Provenance & Evidence