Phenylboronic Acid → HCID 46841855, compound

Participants

Reaction Steps

Phenylboronic acid (0.058 g, 0.48 mmol) and Pd(PPh3)4 (0.004 g) were added to a mixture of 2-(6-bromopyridin-3-yl)-3-(4-sec-butylphenyl)quinazolin-4(3H)-one (0.175 g, 0.40 mmol) in 2 M Na2CO3 (0.4 mL) and DME (15 mL). After refluxing for 5 hours, the reaction mixture was concentrated in vacuo. The residue was dissolved in CHCl3 and washed with H2O, then brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 0% to 60% of EtOAc in CH2Cl2, afforded the title compound as a white solid (0.080 g, 46%). 1H-NMR (300 MHz, DMSO-d6): δ8.75 (s, 1H), 8.68 (s, 1H), 8.23 (d, J=8.0 Hz, 1H), 7.91-7.99 (m, 1H), 7.79-7.90 (m, 2H), 7.61-7.69 (m, 1H), 7.32-7.50 (m, 7H), 7.17-7.25 (m, 2H), 2.52-2.63 (m, 1H), 1.33-1.54 (m, 2H), 1.10 (d, J=6.9 Hz, 3H), 0.53 (t, J=7.3 Hz, 3H). MS (APCI) m/z: 432 (M+H)+.

Provenance & Evidence