Diethyl Ether → HCID 68006769, compound

Participants

Reaction Steps

To a solution of 2-pyridin-4-yl-5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)-1,3-thiazole-4-carbaldehyde (280.0 mg, 0.722 mmol) in tetrahydrofuran (4.0 mL, 40 mmol), 1 M 4-chlorophenyl magnesium bromide in ether (4.0 mL, 4 mmol) was added and the mixture was stirred for 40 min at rt. After the reaction was completed a 5% aqueous solution of NH4Cl (10 mL) and EtOAc (10 mL) were added and the resulting bi-phasic mixture was vigorously stirred for 15 min then the aqueous phase was discarded. The organic phase was washed with brine (5 mL) then dried over anhydrous MgSO4. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (SiO2, elution with 20-80% EtOAc in hexane) to give the title compound as a white solid (230 mg, 73.6%). LCMS: (FA) ES+, 500. 1H NMR (400 MHz, d6-DMSO) δ:8.96 (s, 1H), δ 8.70-8.72 (dd, J=1.75 Hz, 2H), 7.87-7.89 (dd, J=1.75, 2H), 7.32-7.37 (m, 2H), 7.55-7.58 (m, 3H), 6.85-6.87 (d, J=5.5 Hz, 1H), 6.15-6.17 (d, J=5.5 Hz, 1H), 5.6 (s, br, 2H), 3.65-3.67 (m, 2H), 0.850-0.90 (m, 2H), −0.05 (s, 9H).

Provenance & Evidence