Hydrochloric Acid → HCID 118131356, compound

Participants

Reaction Conditions

Reaction Steps

3-(1-(4-Amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-7-methyl-4-phenyl-1H-isochromen-1-one (intermediate D29, 0.100 g, 0.19 mmol), (3-fluoro-5-hydroxyphenyl)boronic acid (0.036 g, 0.229 mmol) and PPh3 (0.030 g, 0.114 mmol) were dissolved in a mixture of DMF (10 ml), EtOH (4 ml) and water (4 ml); Na2CO3 (0.101 g, 0.95 mmol) was added and the mixture was degasses under nitrogen. Pd(OAc)2 (0.009 g, 0.038 mmol) was added and the reaction was heated at 80° C. for 15 min. 1M HCl was added (pH≈2) and the mixture was partitioned between EtOAc and water. The organic phase was extracted with EtOAc and the combined organic layers were washed several times with brine and dried over sodium sulfate. The solvent was removed and the crude was purified by flash chromatography on Biotage silica gel cartridge (DCM to DCM:MeOH=97:3) to afford the title compound (0.023 g, 0.045 mmol, 24%).

Provenance & Evidence