2-Methoxyaniline → 6-chloro-N-(2-methoxyphenyl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-methoxyaniline (0.18 g), 6-chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridine (0.50 g), Cs2CO3 (0.94 g), and (2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) chloride (0.071 g) in toluene (6 mL) was degassed and back filled with nitrogen (3 times) before it was heated at 80° C. for overnight. The reaction was cooled and diluted with ethyl acetate (15 mL) and water (10 mL). The mixture was filtered through celite and the filtrate was separated, the organic layer was wash with with brine (10 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with EtOAc/isohexane=25% to give 6-chloro-N-(2-methoxyphenyl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-amine (380 mg, 77% yield) as a brown solid.

Provenance & Evidence