تفاعل #79006

معادلة التفاعل

NaOH

4-cyano-3-fluoro-bromobenzene

(1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid

sodium carbonate

→

title compound

المردود 6.0%

6-(4-Cyano-3-fluoro-phenyl)-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]-oxazin-2-one

المردود 6.0%

المذيبات

water

ethylene glycol dimethyl ether

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto reflux for 18 hours
2. 2
   استخلاصextracted with EtOAc (3×50 mL)
3. 3
   غسيلThe combined extracts were washed with water, brine
4. 4
   تجفيفdried (MgSO4)
5. 5
   أخرىevaporated
6. 6
   أخرىThe residue was purified by column chromatography (SiO2, EtOAc:hexane=1:2)

الإجراء التجريبي

A solution of 4-cyano-3-fluoro-bromobenzene (0.6 g, 3.0 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.2 g) in ethylene glycol dimethyl ether (20 mL) was stirred under N2 for 20 minutes. To this mixture was then added (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid (1.0 g, 4.5 mmol) and sodium carbonate (1.1 g, 10.6 mmol) in water (5 mL). The solution was brought to reflux for 18 hours and then cooled to room temperature, poured into 2N NaOH and extracted with EtOAc (3×50 mL). The combined extracts were washed with water, brine, dried (MgSO4), and evaporated. The residue was purified by column chromatography (SiO2, EtOAc:hexane=1:2) to afford the title compound (0.05 g, 6%) as an off-white solid. mp: 272-275° C.; 1H-NMR (DMSO-d6) δ 10.4 (s, 1H), 8.0 (t, 1H, J=7.7 Hz), 7.9 (dd, 1H, J=10.3, 1.3 Hz), 7.8 (dd, 1H, J=6.8, 1.4 Hz), 7.7 (m, 2H), 6.9 (d, 1H, J=8.9 Hz), 1.7 (s, 6H); MS (EI) M+ @ m/z 296.

المصدر