反应详情

温度

95 °C

The ligand sodium 2′-dicyclohexylphosphino-2,6-dimethoxy-1,1′-biphenyl-3-sulphonate hydrate (146 mg/0.3 mmol) and the catalyst PdCl2(dppf) (280 mg/0.36 mmol) are added successively, under argon, to a suspension of 6-[4-fluoro-3-(methoxycarbonyl)phenyl]-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid [described in Step 1.7.] (1.5 g/3 mmol), benzyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate [880157-10-8] (1.16 g/3.4 mmol) and potassium carbonate (828 mg/6.0 mmol) in 9.5 mL of DMF. The reaction mixture is heated at 95° C. for 1 h. It is run into a saturated aqueous solution of NaHCO3 and extracted with EtOAc. The organic phase is washed with water and with a saturated aqueous solution of NaCl, dried over sodium sulphate, filtered and concentrated to dryness. After purification by flash chromatography on silica (DCM/EtOH 0.1% TEA: 100/0 to 90/10), 1.31 g of a yellow solid are obtained (triethylamine salt; yield: 72%).

1. extractionextracted with EtOAc
2. washThe organic phase is washed with water and with a saturated aqueous solution of NaCl
3. dry with materialdried over sodium sulphate
4. filtrationfiltered
5. concentrationconcentrated to dryness
6. customAfter purification by flash chromatography on silica (DCM/EtOH 0.1% TEA: 100/0 to 90/10), 1.31 g of a yellow solid
7. customare obtained (triethylamine salt; yield: 72%)