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

Participants

Reaction Conditions

Reaction Steps

Into a 5 mL oven-dried microwave vial was added (R)-BINAP (159 mg, 0.255 mmol) and diacetoxypalladium (13.28 mg, 0.059 mmol). Toluene (2 mL) was added and the solution was stirred at 40° C. for 10 min. Then 7-iodo-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridine (216 mg, 0.592 mmol) in 2 mL of toluene was added, followed by 2-(5-chloro-2-fluorophenyl)pyridin-4-amine (132 mg, 0.592 mmol) and sodium 2-methylpropan-2-olate (85 mg, 0.887 mmol). Nitrogen was sparged into the solution for about 2 minutes, and the reaction was heated in a 100° C. oil bath over night. The reaction mixture was cooled and purified using silica column chromatography (0-5 methanol/dichloromethane) to give a residue. The residue was further purified by silica column chromatography (1:1 Ethyl acetate/hexanes) gave 100 mg of N-(2-(5-chloro-2-fluorophenyl)pyridin-4-yl)-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridin-7-amine. MS [M+H] found 460.3.

Provenance & Evidence