تفاعل #77192

معادلة التفاعل

ethyl 8-chloro-4-oxo-4H-quinolizine-3-carboxylate

Ethyl 8-Chloro-4-oxo-4H-quinolizine-3-carboxylate

4-methoxyphenylboronic acid

CsF

DMF

→

solid

المردود 52.6%

Ethyl 8-(4-Methoxyphenyl)-4-oxo-4H-quinolizine-3-carboxylate

المردود 52.6%

المذيبات

water

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   أخرىAn oven-dried 50 ml round-bottom flask equipped
2. 2
   درجة الحرارةwith reflux condenser
3. 3
   أخرىwas purged with argon
4. 4
   درجة الحرارةcooled to room temperature
5. 5
   استخلاصextracted three times with 100 ml chloroform
6. 6
   غسيلThe combined organic layers were washed three times with 50 ml water
7. 7
   أخرىThe organic solvent was evaporated
8. 8
   أخرىthe crude product was further purified by column chromatography (5% MeOH in ethyl acetate)

الإجراء التجريبي

An oven-dried 50 ml round-bottom flask equipped with reflux condenser was purged with argon, followed by addition of ethyl 8-chloro-4-oxo-4H-quinolizine-3-carboxylate (2) (500 mg, 2 mmol), 4-methoxyphenylboronic acid (372 mg, 2.4 mmol), CsF (600 mg, 3.9 mmol), PdCl2[P(c-Hex)3]2 (80 mg, 0.1 mmol) and 6 ml DMF. The reaction mixture was stirred at 110° C. for 12 h and cooled to room temperature. Completion of the reaction was indicated by thin layer chromatography (ethyl acetate). The reaction mixture was poured into 100 ml water and extracted three times with 100 ml chloroform. The combined organic layers were washed three times with 50 ml water. The organic solvent was evaporated and the crude product was further purified by column chromatography (5% MeOH in ethyl acetate) to give a bright yellow solid (340 mg, 50% yield). M.p. 205-209° C. 1H NMR (δ, CDCl3): 1.43 (t, J=7 Hz, 3H), 3.90 (s, 3H), 4.42 (q, J=7 H, 2H), 6.65 (d, J=8 Hz, 1H), 7.05 (d, J=9 Hz, 2H), 7.43 (dd, J=2 Hz, J=7 Hz, 1H), 7.58-7.80 (m, 3H), 8.37 (d, J=8 Hz, 1H), 9.41 (d, J=7 Hz, 1H). MS: m/z 323.1159; required for C19H17NO4: 323.1157.

المصدر