Triphenylphosphine → HCID 59176341, compound

Participants

Reaction Steps

To a solution of 2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-ol (300 mg, 0.90 mmol) in anhydrous THF (15 ml) were added at ambient temperature under a nitrogen atmosphere triphenylphosphine (352 mg, 1.34 mmol), (1-methylpyrrolidin-3-yl) methanol (155 mg, 1.34 mmol) and diethyl azodicarboxylate (0.21 ml, 1.34 mmol). The reaction mixture was stirred at ambient temperature under nitrogen atmosphere overnight. The mixture was treated with saturated aqueous sodium bicarbonate solution (20 mL) and extracted with CH2Cl2 and EtOAc. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated to afford the crude product. The crude product was purified by column chromatography on silica gel (elution with 10% MeOH/CH2Cl2) to afford partially purified product. This material was purified by silica gel chromatography (eluting with 10% 7N NH3/MeOH/CH2Cl2) to provide the title compound (34.2 mg, 9% yield) as a solid. MS ESI (+) m/z 433.2 (M+1) detected.

Provenance & Evidence