4-Chlorophenylboronic acid → HCID 135510651, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-(2-chlorophenyl)-8-iodo-3H-pyrazolo[1,5-a][1,3,5]-triazin-4-one (I-3A-9d; 500 mg, 1.34 mmol), 4-chlorophenylboronic acid (315 mg, 2.01 mmol), and tetrakis(triphenylphosphine)palladium (50 mg, 0.043 mmol) under an argon atmosphere in ethanol (12 ml) and 2M aqueous Na2CO3 (2.5 ml) was degassed (3×) by pulling a vacuum followed by refilling with argon gas. The mixture was heated at 68° C. for 7 hours and then cooled to room temperature. The mixture was extracted from water with ethyl acetate, the combined organic layers were washed with brine, dried (MgSO4), and concentrated, in vacuo, to afford a dark, viscous oil (690 mg). The product was crystallized from methanol and then collected by vacuum filtration to afford, after rinsing with methanol, intermediate I-3A-9e (218 mg, 45%) as a solid: +APcI MS (M+1) 357.0; 1H NMR (400 MHz, CD3OD) δ 8.02 (s, 1H), 7.54-7.41 (m, 4H), 7.34 (d, J=8.7 Hz, 2H), 7.23 (d, J=8.7 Hz, 2H).

Provenance & Evidence