반응 #77192

반응 방정식

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

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

4-methoxyphenylboronic acid

CsF

DMF

→

solid

수율 52.6%

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

수율 52.6%

용매

water

ethyl acetate

반응 조건

후처리

1. 1
   기타An oven-dried 50 ml round-bottom flask equipped
2. 2
   온도with reflux condenser
3. 3
   기타was purged with argon
4. 4
   온도cooled to room temperature
5. 5
   추출extracted three times with 100 ml chloroform
6. 6
   세척The combined organic layers were washed three times with 50 ml water
7. 7
   기타The organic solvent was evaporated
8. 8
   기타the crude product was further purified by column chromatography (5% MeOH in ethyl acetate)

실험 절차

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.

출처