反应详情

A mixture of the product from Example 114A (2.2 g, 7.5 mmol), phenylboronic acid (919 mg, 7.5 mmol), sodium carbonate (7.55 mL, 2 M aqueous solution, 15.1 mmol) tetrakis(triphenylphosphine)palladium(0) (261 mg, 0.23 mmol) and 50 mL of toluene were refluxed for 16 hours under nitrogen. The reaction was cooled and partitioned between 50 mL of water and 50 mL of ethyl acetate. The aqueous portion was separated and extracted with 2×25 mL of ethyl acetate and the combined organic extracts were washed with 2×25 mL of water and 1×25 mL of brine and dried over sodium sulfate. The organic solution was concentrated and the residue was purified via flash chromatography on a silica gel column (95:5 hexane:ethyl acetate) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.63 (s, 3H) 7.35-7.60 (m, 6H) 7.71-7.79 (m, 2H); MS (DCI+) m/z 308.0 [M+NH4]+.

1. temperaturewere refluxed for 16 hours under nitrogen
2. temperatureThe reaction was cooled
3. custompartitioned between 50 mL of water and 50 mL of ethyl acetate
4. customThe aqueous portion was separated
5. extractionextracted with 2×25 mL of ethyl acetate
6. washthe combined organic extracts were washed with 2×25 mL of water and 1×25 mL of brine
7. dry with materialdried over sodium sulfate
8. concentrationThe organic solution was concentrated
9. customthe residue was purified via flash chromatography on a silica gel column (95:5 hexane:ethyl acetate)