反应详情

温度

100 °C

To a solution of 10-Bromo-9-chloro-2,3-dihydro-[1,4]dioxino[2,3-f]quinoline (11.5 g, 38.4 mmol, 1 eq) in DME (425 mL, degassed with Argon), was added Pd(PPh3)4, the reaction was stirred under Argon for 20 mins. Water (122 mL), K2CO3 (5.32 g, 38.4 mmol, 1 eq) and the 2,4,6-trivinylcyclotriboroxane-pyridine complex (2.49 g, 15.4 mmol, 0.4 eq) were added, the mixture was then heated to reflux at 100° C. overnight. The reaction was then cooled, the product was extracted with water and DCM, dried over Na2SO4, filtered and evaporated to dryness. The solid obtained was the passed through silica with as a pale yellow solid (5.5 g, 58%). LC/MS (ES) m/z 247 (MH+ 100%); 1H-NMR (400 MHz, CDCl), 8.69 (1H, s, CHNHC), 7.59 (1H, d, J=9.2, CHCO), 7.18 (1H, dd, J=18, 12, CCH═C), 5.68 (1H, dd, J=12, 1, Hcis of CH2=C), 5.49 (1H, dd, J=18, 1, H trans of CH2=C), 4.37-4.339 (4H, m, 2×(CH2O)).

1. temperaturethe mixture was then heated
2. temperatureThe reaction was then cooled
3. extractionthe product was extracted with water and DCM
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. customevaporated to dryness
7. customThe solid obtained