反应详情

温度

90 °C

A mixture of 2-bromo-4-(4-hydroxy-piperidin-1-yl)-benzoic acid methyl ester (1.2 g, 3.82 mmol), phenylboronic acid (800 mg; 6.56 mmol), potassium phosphate, tribasic, mono-hydrate (1.3 g, 10.7 mmol), and tetrakis(triphenylphosphine)palladium (500 mg, 0.433 mmol) in 1,2-dimethoxyethane (25 mL) and water (1 mL) is heated to 90° C. under a nitrogen atmosphere for 24 h. The mixture is concentrated and partitioned between ethyl acetate and water. The solvent layers are separated and the aqueous layer is extracted with ethyl acetate (3×). The combined ethyl acetate layers are dried (MgSO4), filtered, and concentrated under reduced pressure. The residue is purified on silica (120 g) eluting with a gradient of 0% to 100% ethyl acetate in heptane to provide the desired product (1.09 g, 92%) as a gummy residue. LC-ES/MS m/z 312.0 (M+1)

1. concentrationThe mixture is concentrated
2. custompartitioned between ethyl acetate and water
3. customThe solvent layers are separated
4. extractionthe aqueous layer is extracted with ethyl acetate (3×)
5. dry with materialThe combined ethyl acetate layers are dried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe residue is purified on silica (120 g)
9. washeluting with a gradient of 0% to 100% ethyl acetate in heptane