Triphenyl[(pyridin-2-yl)methyl]phosphanium chloride--hydrogen chloride (1/1/1) → HCID 50915291, compound

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Reaction Steps

To a solution containing triphenyl(2-pyridylmethyl)phosphonium chloride hydrochloride (153 mg, 0.359 mmol) in tetrahydrofuran (2.26 ml) at −78° C. was added n-butyl lithium (2.50 M, 0.685 mmol). This mixture was stirred for 15 min. and then added to a solution containing 6-bromo-2-oxo-3-(thiophen-2-yl)-1,2-dihydroquinoline-4-carbaldehyde (109 mg, 0.326 mmol) in tetrahydrofuran (1 ml) at −78° C. The reaction was allowed to stir for 4 h at room temperature. The reaction was quenched with 1 N hydrochloric acid (10 ml) and then the pH was increased with 1 N sodium hydroxide. This mixture was extracted with ethyl acetate (3×30 ml). The organic layers were combined and extracted with sodium chloride (1×25 ml). The organic layer was then dried over magnesium sulfate, filtered and concentrated. The resulting crude solid was purified by reverse phase chromatography to afford 6-bromo-4-[(E)-2-(pyridine-2-yl)ethenyl]-3-(thiophen-2-yl)quinolin-2(1H)-one as a yellow solid. LCMS (M+H)=410.69. 1H NMR (400 MHz, d6-DMSO) δ 12.28 (s, 1H), 8.63-8.60 (m, 1H), 7.95 (d, 1H), 7.85 (m, 1H), 7.74-7.65 (m, 3H), 7.60 (d, 1H), 7.39-7.33 (m, 3H), 7.09 (dd, 1H), 6.99 (d, 1H).

Provenance & Evidence