Binap, (A+-)- → N-(2-(5-chloro-2-fluorophenyl)pyridin-4-yl)-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridin-7-amine

Participants

Reaction Conditions

Reaction Steps

(R)-BINAP (0.808 g, 1.298 mmol), diacetoxypalladium (0.068 g, 0.301 mmol) and Toluene (10 mL) was added to a round bottom flask and the solution was stirred at 40° C. for 10 minutes. This mixture was removed from heat and a suspension of 7-iodo-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridine (1.1 g, 3.01 mmol), 2-(5-chloro-2-fluorophenyl)pyridin-4-amine (0.671 g, 3.01 mmol) and sodium 2-methylpropan-2-olate (0.434 g, 4.52 mmol) in toluene (11 mL) was added. The reaction mixture was sparged with nitrogen and heated at 100° C. overnight. The reaction mixture was cooled to room temperature, concentrated in-vacuo and purified on a silica gel column chromatography (Ethyl acetate/hexanes 1:1) to give as a mixture N-(2-(5-chloro-2-fluorophenyl)pyridin-4-yl)-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridin-7-amine and N-(2-(5-chloro-2-fluorophenyl)pyridin-4-yl)-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridin-7-amine as a yellow foam; MS [M+H] found 460.3.

Provenance & Evidence