Boron tribromide → HCID 66782170, compound

Participants

Reaction Conditions

Reaction Steps

To a flask containing 8-(-3-fluoropiperidin-4-yloxy)-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinoline (Prepared according to Example 20; 0.062 g, 0.14 mmol) was added CH2Cl2 (14 mL) and the solution was cooled to −78° C. BBr3 (1.0M in CH2Cl2, 0.71 ml, 0.71 mmol) was added dropwise and the reaction stirred at −78° C. for 1 hour, then slowly warmed to 0° C. over 2.0 hours, then warmed to ambient temperature and stirred for 0.5 hours. The reaction was quenched by the addition of a saturated aqueous NaHCO3 solution (15 mL) and the layers were separated. The aqueous phase was extracted with CH2Cl2 and the combined organic phases were washed with brine and dried over Na2SO4. The mixture was filtered and concentrated in vacuo and purified via column chromatography (6% NH4OH in MeOH/CH2Cl2, 2% to 20% linear gradient) to afford 0.015 g (0.25%) of the title compound as a solid. MS APCI (+) m/z 423.2 [M+H]+ detected.

Provenance & Evidence