反应详情

温度

120 °C

6′-Methoxy-5′,7′,8′-trimethyl-1′H-spiro[cyclobutane-1,3′-quinolin]-4′(2′H)-one (146.7 mg), palladium (II) acetate, 1-chloro-4-iodobenzene (202.5 mg) and NaO-t-Bu (81.6 mg) were added to an oven dried tube. The flask was capped and the air evacuated with a house vacuum line, then refilled with nitrogen. This nitrogen flushing was repeated 3 times. Toluene (1.5 mL) was then added and the suspension was stirred for 15 min at room temperature before ter-butylphosphine (1.7 mL, 0.056 mmol, 33.7 mM in toluene) was added. The mixture was then heated up in oil bath (120° C.) for 2.5 h. It was then quenched with water and extracted with ethylacetate. The organic phase was washed with brine, dried and evaporated to give an oil, which was passed through a silica column (EtOAc/Hexane: 0-10%) to give 1′-(4-chlorophenyl)-6′-methoxy-5′,7′,8′-trimethyl-1′H-spiro[cyclobutane-1,3′-quinolin]-4′(2′H)-one (137.6 mg) as a solid. 1H-NMR (300 MHz, CDCl3) δ=7.257-7.026 (d, 2H), 6.904-6.553 (d, 2H), 4.09 (s, 2H), 3.71 (s, 3H), 2.62 (s, 3H), 2.454-2.276 (m, 2H), 2.24 (s, 3H), 2.125-1.836 (m, 2H), 1.81 (s, 3H), 1.746-1.554 (m, 2H) ppm. 13CNMR (75 MHz, CDCl3) δ=201.17, 148.99, 144.28, 137.51, 131.65, 129.92, 129.28, 125.56, 125.37, 121.03, 60.28, 60.04, 50.71, 9.71, 15.57, 15.44, 14.63, 13.92 ppm.

1. customdried tube
2. customThe flask was capped
3. customthe air evacuated with a house vacuum line
4. additionrefilled with nitrogen
5. additionToluene (1.5 mL) was then added
6. additionwas added
7. customIt was then quenched with water
8. extractionextracted with ethylacetate
9. washThe organic phase was washed with brine
10. customdried
11. customevaporated
12. customto give an oil, which