Sodium Carbonate → HCID 69093177, compound

Participants

Reaction Steps

A mixture of intermediate I-25 (6.11 g, 89% pure, 18.86 mmol), 2,4-difluorophenyl-boronic acid (4.55 g, 28.86 mmol), LiCl (3.26 g, 1.41 mmol), Na2CO3 (8.1 g, 76.46 mmol), in DME (70.2 mL) and H2O (38 mL) was deoxygenated with a nitrogen flow. Then, tetrakis(triphenylphosphine)palladium (0) (1.63 g, 1.41 mmol) was added and the mixture was stirred under nitrogen atmosphere, at reflux for 5 hours. After cooling, the mixture was diluted with EtOAc/H2O and filtered off over diatomaceous earth. The filtrate was washed with saturated NaHCO3 and extracted with EtOAc. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by two flash column chromatographies (silica; EtOAc in heptane 0/100 to 5/95, then silica; CH2Cl2 100%). The desired fractions were collected and concentrated in vacuo to yield intermediate I-26 (1.56 g, 32.7%) as oil.

Provenance & Evidence