反应详情

温度

105 °C

6′-Methoxy-7′,8′-dimethyl-1′H-spiro[cyclobutane-1,3′-quinolin]-4′(2′H)-one (300 mg) was mixed with 1-chloro-4-iodobenzene (465 mg), NaOtBu (187.4 mg) and [PdBr(tBu3P)2]2 (20 mg). The reaction tube was then sealed with rubber septum, the air was evacuated, then it was flushed with nitrogen. This process was repeated three times, and then toluene (1.5 mL) was added. The reaction tube was then heated in a 105° C. bath for 2 hours. The mixture was then cooled, quenched with water, and extracted with EtOAc. The organic phase was washed with brine, dried and evaporated to give a crude mixture, that was eluted on a silica column (Hexane: EtOAc; 10:1.5-10:2) to give 1′-(4-chlorophenyl)-6′-methoxy-7′,8′-dimethyl-1′H-spiro[cyclobutane-1,3′-quinolin]-4′(2′H)-one (285 mg) as a yellow solid. 1H-NMR (300 MHz, CDCl3) δ=7.399 (s, 1H), 7.16-7.09 (m, 2H), 6.81-6.73 (m, 2H), 4.07 (s, 2H), 3.86 (s, 3H), 2.36-2.23 (m, 2H), 2.13 (s, 3H), 1.99-1.78 (m, 1H), 1.76 (s, 3H), 1.69-1.42 (m, 3H) ppm. 13C-NMR (75 MHz, CDCl3) δ=198.29, 154.39, 149.44, 141.4, 134.46, 132.07, 129.25, 125.87, 124.07, 121.47, 105.15, 60.96, 55.62, 48.86, 28.59, 15.55, 15.52, and 13.09 ppm.

1. customThe reaction tube was then sealed with rubber septum
2. customthe air was evacuated
3. customit was flushed with nitrogen
4. additiontoluene (1.5 mL) was added
5. temperatureThe mixture was then cooled
6. customquenched with water
7. extractionextracted with EtOAc
8. washThe organic phase was washed with brine
9. customdried
10. customevaporated
11. customto give a crude mixture, that
12. washwas eluted on a silica column (Hexane: EtOAc; 10:1.5-10:2)