Sodium Bicarbonate → US10023592, Example 368

Participants

Reaction Steps

To a microwave vial containing 5-bromo-7-methylimidazo[1,5-a]pyrazin-8-one (150 mg, 0.66 mmol), 2-[2-(cyclopropylmethoxy)-5-ethylsulfonylphenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (290 mg, 0.80 mmol) and NaHCO3 (1 mL, 2M) in dioxane (3 mL) was added Pd(dppf)Cl2 (80 mg, 0.10 mmol). The mixture was purge with N2 for 2 min and sealed. The reaction was irradiated in microwave at 100° C. for 2 h. Water (20 mL) was added and the mixture was extracted with EtOAc (20 mL×3). The combined organic layers were washed with brine (20 mL), dried with Na2SO4, filtered and concentrated in vacuum. The residue was purified by column chromatography (PE: EA=5:1 to 1:1) to afford the title compound (55.3 mg, 22%) as a light yellow solid. 1H NMR (CDCl3, 400 MHz) δ 8.03 (dd, J1=8.4 Hz, J2=2.0 Hz, 2H), 7.94 (d, J=2.0 Hz, 1H), 7.56 (s, 1H), 7.15 (d, J=8.8 Hz, 1H), 6.49 (s, 1H), 3.96 (d, J=6.4 Hz, 2H), 3.54 (s, 3H), 3.16 (q, J=7.6 Hz, 1H), 1.33 (t, J=7.6 Hz, 1H), 1.08 (s, 1H), 0.54 (d, J=7.2 Hz, 2H), 0.54 (d, J=4.4 Hz, 2H). LCMS: 388.1 (M+1)+

Provenance & Evidence