Water → Tert-butyl 2-((2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)methyl)morpholine-4-carboxylate

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Reaction Conditions

Reaction Steps

To a solution of 2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-ol [prepared as in Example 3, Step C; 50 mg, 0.15 mmol] in anhydrous DMA (2 mL) was added cesium carbonate (150 mg, 0.45 mmol) followed by tert-butyl 2-((methylsulfonyloxy)methyl)morpholine-4-carboxylate (130 mg, 0.45 mmol). The heterogeneous mixture was stirred at 100° C. for 16 hours and allowed to cool. The mixture was treated with water (20 mL) and extracted with EtOAc. The combined organic phases were washed with water and brine, then dried over Na2SO4, filtered and concentrated. The residue was purified via flash column chromatography using gradient elution (CH2Cl2 to 1% MeOH/CH2Cl2 to 2% MeOH/CH2Cl2) to afford tert-butyl 2-((2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)methyl)morpholine-4-carboxylate as a gum. This was dissolved in CH2Cl2 (4 mL) and treated with TFA (1 mL). After stirring for 2 hours at ambient temperature the mixture was concentrated. The residue was triturated with ether, filtered and dried in vacuo to provide 29.1 mg (76%) of desired product as its di-TFA salt as a powder. MS ESI (+) m/z 435.3 (M+1) detected.

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