Potassium Carbonate → 8-Bromo-2-(1-phenylvinyl)quinazoline

関与物質

反応条件

反応手順

A suspension of 8-bromo-2-chloroquinazoline (Ark Pharm, Inc., Libertyville, Ill.; 2.00 g, 8.21 mmol), (1-phenylvinyl)boronic acid (Aldrich; 1.215 g, 8.21 mmol), potassium carbonate (2.384 g, 17.25 mmol), and Pd(PPh3)4 (0.190 g, 0.164 mmol) in toluene (75 mL) was stirred under argon at 90° C. for 2.5 d. The reaction was cooled to 25° C. and partitioned between EtOAc (200 mL) and water (100 mL). The organic layer was separated, sequentially washed with water (2×80 mL) and brine (80 mL), dried over Na2SO4, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0-100% hexanes/DCM) furnished 8-bromo-2-(1-phenylvinyl)quinazoline (380 mg, 1.221 mmol, 15% yield) as a yellow solid: 1H NMR (400 MHz, CDCl3) δ ppm 9.36 (1H, s), 8.20 (1H, s), 7.88 (1H, d, J=8.0 Hz), 7.58-7.65 (2H, m), 7.44-7.51 (2H, m), 7.40-7.44 (2H, m), 6.84 (1H, s), 5.99 (1H, s). m/z (ESI, +ve) 311.0 (M+H)+.

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