5-(Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbaldehyde → HCID 86627823, compound

Participants

Reaction Conditions

Reaction Steps

5-bromo-3-[5-trifluoromethoxy-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridine Compound 16e (0.12 g, 0.18 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine-3-carbaldehyde Compound 15b (0.063 g, 0.27 mmol) and 2M Na2CO3 (5 drops) were mixed in DME (10 mL) in a reaction tube. The resulting yellowish clear solution was degassed with nitrogen for 15 minutes, then tetrakis(triphenylphosphine)palladium(0) (0.021 g, 0.018 mmol) was added and the reaction tube was sealed and heated at 100° C. overnight. The sealed tube was cooled and opened and the contents was diluted with DCM and H2O, then filtered through Celite. The solvent was evaporated to dryness to provide 5-[3-[5-trifluoromethoxy-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-pyridine-3-carbaldehyde Compound 17a (0.241 g) as a brown semi-solid which was used directly in the next step without further purification. LCMS single peak, 4.614 min, MS (ESI) m/z 685.2 (M+H+).

Provenance & Evidence