反应详情

Place 3-(ethoxycarbonyl)phenylboronic acid (670 mg, 3.46 mmol), 3-(3-bromo-2,6-dichlorobenzyl)-1-cyclohexylpyrrolidin-2-one (Example 50) (700 mg, 1.73 mmol), and Pd(PPh3)4 (173 mg, 0.173 mmol) into a flask and purge with nitrogen. Add DME (50 mL) and 2M sodium carbonate (5 mL) and heat to 75° C. for 24 hr. Cool reaction, add DCM and wash with saturated sodium bicarbonate. Dry, filter, and concentrate organic layer. Purify by silica gel (30-45% EtOAc in Hex). Dissolve ester in ethanol (3 mL) and water (1 mL) and add KOH (291 mg, 5.18 mmol. Stir for 1 hour at room temperature. Strip off solvent and add water. Bring to a pH of 2 with 1M HCl. Filter precipitate to give 727 mg (94%) of title compound as a white solid. Mass spectrum (apci) m/z=446.2 (M+H).

1. temperatureCool
2. customreaction
3. washwash with saturated sodium bicarbonate
4. customDry
5. filtrationfilter
6. concentrationconcentrate organic layer
7. customPurify by silica gel (30-45% EtOAc in Hex)
8. additionDissolve ester in ethanol (3 mL) and water (1 mL) and add KOH (291 mg, 5.18 mmol
9. additionStrip off solvent and add water
10. filtrationFilter precipitate