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ethyl 8-[(3-fluoropyridin-2-yl)methoxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylate trifluoroacetate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
68%
Ethyl 8-[(3-fluoropyridin-2-yl)methoxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylate trifluoroacetate 144 mg of ethyl 8-hydroxy-2-methylimidazo[1,2-a]pyridine-3-carboxylate (Example 3A, 0.65 mmol) were dissolved in 3.9 ml of THF, and 100 mg of <strong>[31181-79-0](3-fluoropyridin-2-yl)methanol</strong> (0.79 mmol), 189 mg of triphenylphosphine (0.72 mmol) and then 0.15 ml of diisopropyl azodicarboxylate (0.72 mmol) were added. The reaction mixture was stirred at RT overnight and then purified by preparative HPLC (RP18 column, mobile phase: acetonitrile/water gradient with addition of 0.1percent TFA). This gave 198 mg (68percent of theory, purity 99percent) of the target compound. LC-MS (Method 1): Rt=0.84 min
With cyanomethylenetributyl-phosphorane; In toluene; at 110℃; for 2h;
Preparation Example 3 (0260) A mixture of 2 g of ethyl 8-hydroxy-2-methylimidazo[1,2-a]pyridine-3-carboxylate, 2 g of <strong>[31181-79-0](3-fluoropyridin-2-yl)methanol</strong>, 4 g of (tributylphosphoranyliden)acetonitrile, and 40 ml of toluene was stirred at 110° C. for 2 hours. The reaction mixture was concentrated under reduced pressure, water was added thereto, and the precipitated solid was collected by filtration. The obtained residue was purified by silica gel column chromatography to obtain 2.15 g of ethyl 8-[(3-fluoropyridin-2-yl)methoxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylate.
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