Pyridine → HCID 178520623, compound

Participants

Reaction Steps

Oxalyl chloride (0.1 mL, 1.2 mmol) was added to a solution of 5-bromovaleric acid (86 mg, 0.48 mmol) in dichloromethane (10 mL). N,N-Dimethylformamide (1 drop) was added and the mixture was stirred at ambient temperature for 16 hours. The solvent was removed under vacuum, the residue was azeotroped with toluene (3×30 mL) and evaporated to dryness. To this crude acid chloride was added 5-phenyl-1H-pyrazolo[3,4-b]pyridin-3-ylamine (Description 2; 100 mg, 0.48 mmol), pyridine (20 mL). and 4-dimethylaminopyridine (cat). The solution was refluxed at 120° C. for 16 hours then evaporated. The residual material was purified by preparative HPLC on a C18 column, using a gradient elution with 10–90% v/v of acetonitrile (containing 0.01% v/v trifluoroacetic acid) and water (containing 0.1% v/v trifluoroacetic acid) to afford the title compound.

Provenance & Evidence