反应详情

温度

80 °C

A round bottom flask was charged with 0.5 g (1.67 mmol) of Compound 14D, 0.58 g (2,5 mmol) of 2-trifluoromethoxy-5-formylphenylboronic acid and 0.083 g of tetrakis(triphenylphosphine)palladium(0). The flask was sealed with a septa and 8.5 mL of toluene and 2.5 mL of ethanol was added. The resulting solution was stirred to dissolve the reactants and then 1.7 mL of 2M K2CO3 was added via syringe. The reaction mixture was heated to 80° C. for 4 hours. After cooling, the reaction mixture was partitioned between ethyl acatate (20 mL) and water (8 mL). The water layer was further extracted (2×10 mL) and the combined organic layers were washed with water (10 mL) followed by brine (10 mL), dried over magnesium sulfate, filtered and excess solvent removed on the rotary evaporator. The crude product was purified by flash chromatography (EtOAc/Hexanes; gradient 20% to 40%) to give 0.35 g (52%) of 3-(1-ethyl-4,4,6-trimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-7-yl)-4-trifluoromethoxy-benzaldehyde as yellow solid. MS (electrospray): mass calculated for C21H20F3NO4, 407.13; m/z found 408 [M+H]+.

1. additionwas added
2. dissolutionto dissolve the reactants
3. temperatureAfter cooling
4. customthe reaction mixture was partitioned between ethyl acatate (20 mL) and water (8 mL)
5. extractionThe water layer was further extracted (2×10 mL)
6. washthe combined organic layers were washed with water (10 mL)
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. customexcess solvent removed on the rotary evaporator
10. customThe crude product was purified by flash chromatography (EtOAc/Hexanes; gradient 20% to 40%)