Hydrochloric Acid → HCID 118131428, compound

Participants

Reaction Conditions

Reaction Steps

In a sealed vial, a mixture of 3-(1-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-6-fluoro-4-phenyl-1H-isochromen-1-one (intermediate D32, 0.240 g, 0.455 mmol), (3-fluoro-5-hydroxyphenyl)boronic acid (0.156 g, 1 mmol) and K2CO3 (0.138 g, 1 mmol) in dioxane/H2O 4:1 (10 ml) was degassed; Pd(dppf)Cl2 (0.04 g, 0.054 mmol) was added and the reaction was heated at 120° C. for 4 hrs. 1M HCl was added (pH≈1) and the mixture was partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc and the combined organic layers were washed with brine and dried over sodium sulfate. The solvent was removed and the crude was purified by flash chromatography on Biotage silica gel cartridge (cyclohexane:EtOAc=95:5 to =20:80) and then triturated with ACN to yield title compound as a white solid (0.08 g, 0.16 mmol).

Provenance & Evidence