Benzyltriphenylphosphonium bromide → HCID 86676501, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of benzyltriphenylphosphonium bromide (176 mg, 0.406 mmol) in dry THF cooled at 0° C. under inert atmosphere was added potassium tot-butoxide (1.0M in THF) (675 μL, 675 μmol). The mixture was stirred at 0° C. for 30 mins, then 5-[6-(4-methyl-pyridin-2-ylamino)-pyridin-2-yl]-thiazole-2-carbaldehyde was added in one portion. After stirring at room temperature for 3 hours, the reaction mixture was treated with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure before purification by column chromatography on SiO2 using combiflash Companion®, eluting with cyclohexane/ethyl acetate. The E-isomer was then further purified by preparative chromatography on silica plate, eluting with 5% methanol in dichloromethane to afford the title compound as a yellow solid. 1H NMR (Acetone-d6, 300 MHz): δ=8.41 (s, 1H), 8.16 (d, J=5.1 Hz, 1H), 8.00 (s, 1H), 7.80-7.70 (m, 3H), 7.65-7.55 (m, 2H), 7.53-7.36 (m, 4H), 7.50 (s, 1H), 6.84 (d, J=5.1 Hz, 1H), 2.47 (s, 3H). (APCI+) m/z 371 (M+H)+.

Provenance & Evidence