Cesium carbonate → (trans)-Naphthalen-2-ylmethyl 3-hydroxy-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)pyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Cs2CO3. (0.2201 g, 1.141 mmol) was added to a solution of 2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-ol (0.294 g, 0.878 mmol) and (cis)-naphthalen-2-ylmethyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (0.260 g, 0.966 mmol) in DMF (4.5 mL). The reaction was heated to 100° C. overnight, then cooled and poured into 30 mL of ice water. This mixture was extracted with 25%. IP A in CH2Cl2, and the organic layer was dried over sodium sulfate and condensed. The residue was purified by silica gel chromatography, eluting with gradient from 1% to 25% MeOH (with 6% NH4OH) in EtOAc, to collect 223 mg of the desired product. MS APCI (+) m/z 605.1 (M+1) detected.

Provenance & Evidence