反应详情

温度

125 °C

To a microwave vial were added 6-fluoro-3-iodo-2-phenyl-chromen-4-one (55 mg, 0.15 mmol), {1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (62 mg, 0.165 mmol, prepared as described in WO2008/070016), sodium carbonate solution (2M in water, 0.26 mL, 0.53 mmol), tetrakis(triphenylphosphine)palladium(0) (17 mg, 0.015 mmol) and DME (3 mL). The reaction mixture was purged using argon and heated in a microwave reactor to 125° C. for 30 min. The mixture was partitioned between water (2 mL) and EtOAc (3 mL). The aqueous phase was extracted with ethyl acetate (3 mL). The combined organic extracts were washed with brine (5 mL), dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0 to 30% ethyl acetate in cyclohexane) to afford the title compound (22 mg, 30%). 1H NMR (400 MHz, CDCl3): δ 7.95-7.90 (m, 1H), 7.57-7.52 (m, 1H), 7.46-7.30 (m, 6H), 7.28-7.22 (m, 2H), 7.21-7.16 (m, 2H), 5.03 (s, 1H), 2.64-2.31 (m, 4H), 2.14-2.00 (m, 1H), 1.89-1.77 (m, 1H), 1.48-1.18 (m, 9H).

1. customThe reaction mixture was purged
2. customThe mixture was partitioned between water (2 mL) and EtOAc (3 mL)
3. extractionThe aqueous phase was extracted with ethyl acetate (3 mL)
4. washThe combined organic extracts were washed with brine (5 mL)
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo