Sodium Carbonate → HCID 68006677, compound

Participants

Reaction Conditions

Reaction Steps

Into a sealed tube was added potassium vinyltrifluoroborate (1.34 g, 10.0 mmol), 1,4-dioxane (21.0 mL, 269 mmol), 4-[4-bromo-5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)-1,3-thiazol-2-yl]pyridine (2.0 g, 4.6 mmol) and 2 M sodium carbonate in water (9.10 mL, 18.2 mmol). The reaction was degassed with nitrogen for 15 min then tetrakis(triphenylphosphine)palladium(0) (527 mg, 0.456 mmol) was added. The tube was sealed and the reaction was heated in an oil bath at 110° C. with stirring overnight. The reaction solution was cooled to room temperature, water (10 mL) and EtOAc (10 mL) were added, and the combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The obtained residue was purified by column chromatography (SiO2, elution with 0-10% MeOH in DCM) to give the title compound as a yellow solid (1.34 g 81%). LCMS: (FA) ES+ , 386. 1H NMR (400 MHz, d6-DMSO) δ: 8.92 (s, 1H), δ 8.74-8.76 (dd, J=1.75 Hz, J=1.5 Hz 2H), 7.96-7.98 (dd, J=1.75 Hz, 2H), 6.34-6.40 (dd, J=2.3 Hz, 12H), 5.62-5.65 (dd, J=2.3 Hz, 1H), 5.60 (s, br, 2H), 3.63-3.68 (m, 2H), 0.86-0.90 (m, 2H), −0.04 (s, 9H).

Provenance & Evidence