Sodium Carbonate → HCID 89544211, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-bromo-7-(4-methoxybenzyl)imidazo[1,5-a]pyrazin-8(7H)-one (0.167 g, 0.5 mmol (prepared according to Mukaiyama, H. et al., Bioorg. Med. Chem. 2007, 15, 868-885)), tetrakis(triphenylphosphine)palladium (0.06 g, 0.05 mmol) and (5-chloro-2-hydroxyphenyl)boronic acid in dioxane (3 mL) was added 2 M aqueous sodium carbonate (0.75 mL, 1.5 mmol). The reaction mixture was heated at 120° C. for 20 h and was allowed to cool to ambient temperature. The mixture was diluted with ethyl acetate (20 mL), filtered through a pad of sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography eluting with a 0-100% gradient of ethyl acetate in hexanes to afford 5-(5-chloro-2-hydroxyphenyl)-7-(4-methoxybenzyl)imidazo[1,5-a]pyrazin-8(7H)-one as an off-white solid in 66% yield (0.126 g): 1H NMR (300 MHz, acetone-d6) δ9.26 (br s, 1H), 7.78 (s, 1H), 7.70 (s, 1H), 7.39 (m, 4H), 7.05 (dd, J=7.7, 1.5 Hz, 1H), 6.92 (s, 1H), 6.87 (d, J=8.6 Hz, 2H), 5.05 (s, 2H), 3.74 (s, 3H); MS (ES+) m/z 382.0 (M+1), 383.9 (M+1).

Provenance & Evidence