3-Nitrophenylboronic Acid → HCID 58019948, compound

Participants

Reaction Conditions

Reaction Steps

Into a 40 mL vial were added 1-[2-(3-bromo-4-methoxy-phenyl)-ethyl]-1H-pyridin-2-one (I-166, 210 mg, 0.68 mmol), 3-nitrophenylboronic acid (125 mg, 0.75 mmol), PPh3 (36 mg, 0.014 mmol), potassium carbonate (283 mg, 2.04 mmol), dimethoxyethane (10 mL), ethanol (1 mL), and water (1 mL). The suspension was degassed with N2 for 5 minutes and then palladium(II) acetate (15 mg, 0.068 mmol). After degassing for an additional 2 minutes the reaction was stirred at 80° C. for 18 hours. To the reaction was added 5 mL of water and 10 mL of ethyl acetate. The layers were separated and the aqueous was extracted with ethyl acetate (3×10 mL). The organics were combined and concentrated. The residue was purified by flash column chromatography eluting with 10-20% acetone/dichloromethane. The yellow oil which was obtained (136 mg) was dissolved in 1 mL of ether and allowed to stand at room temperature for 3 days. The tan solid which formed was filtered, washed with ether, and dried to afford 74 mg of P-244 in 31% yield. 1H NMR (400 MHz, CDCl3) δ 8.30-8.29 (m, 1H), 8.18-8.15 (m, 1H), 7.81-7.79 (m, 1H), 7.54 (t, J=8.0 Hz), 7.37-7.33 (m, 1H), 7.19 (dd, J=8.2, 2.2 Hz, 1H), 7.05 (d, J=2.4 Hz, 1H), 6.95-6.93 (m, 2H), 6.61 (d, J=9.2 Hz, 1H), 6.06 (td, J=6.6, 1.2 Hz, 1H), 4.15 (t, J=7.0 Hz, 2H), 3.82 (s, 3H), 3.07 (t, J=7.0 Hz, 2H) ppm. LC/MS=99.4%, 351.6 (ESI+).

Provenance & Evidence