Diisoamylamine → 2-(p-Bromophenyl)pyrazolo[1,5-a]pyridine-5-carboxylic diisopentylamide

Participants

Reaction Steps

2-(4-bromophenyl)pyrazolo[1,5-a]pyridine-5-carboxylic acid (2.20 g, 7.0 mmol), diisopentylamine (2.13 mL, 1.64 g, 10.4 mmol) and hydroxybenzotriazole hydrate (1.59 g, 10.4 mmol) were dissolved in DMF (50 mL) and CH2Cl2 (25 mL) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.0 g, 10.4 mmol) was added and the mixture was stirred at room temperature overnight. A saturated solution of ammonium chloride (20 mL) was added and the mixture was diluted with dichloromethane (20 mL). The separated aqueous layer was then extracted with dichloromethane (3×25 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to afford a residue which was purified by column chromatography using 20% to 30% EtOAc in hexanes as eluant to provide 2.89 g of the title compound. LCMS m/z 456.2, 4582 (M+H)+, ret. time=3.33 min.

Provenance & Evidence