反应详情

温度

50 °C

To a nitrogen purged aqueous solution of sodium carbonate (2M, 14 mL) and ethylene glycol dimethyl ether (25 mL) was added 4-chloro-2-iodoanisole (2.50 g, 0.00931 mol), 2-chloropyridine-4-boronic acid (1.61 g, 0.0102 mol) and bis(triphenylphosphine)palladium (II) dichloride (327 mg, 0.00047 mol). The reaction mixture was warmed to 50° C. and stirred for 5 hours. Following LCMS analysis the reaction was warmed to 75° C. and stirred for 5 hours before cooling to room temperature. The reaction was partitioned between ethyl acetate (100 mL) and a 10% w/v aqueous solution of citric acid (50 mL). The organic layer was washed with water (50 mL), dried over anhydrous magnesium sulphate, filtered and the solvents removed in vacuo to give the crude product as an orange oil (2.95 g). The material was purified using an ISCO™ companion (120 g column, eluting with 100% heptane to 7:3 heptane/ethyl acetate). Fractions containing product were combined and concentrated in vacuo to obtain the title compound as an off white solid (1.10 g).

1. temperatureFollowing LCMS analysis the reaction was warmed to 75° C.
2. stirringstirred for 5 hours
3. temperaturebefore cooling to room temperature
4. customThe reaction was partitioned between ethyl acetate (100 mL)
5. washThe organic layer was washed with water (50 mL)
6. dry with materialdried over anhydrous magnesium sulphate
7. filtrationfiltered
8. customthe solvents removed in vacuo
9. customto give the crude product as an orange oil (2.95 g)
10. customThe material was purified
11. washan ISCO™ companion (120 g column, eluting with 100% heptane to 7:3 heptane/ethyl acetate)
12. additionFractions containing product
13. concentrationconcentrated in vacuo