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

Participants

Reaction Conditions

Reaction Steps

(R)-BINAP (1.102 g, 1.770 mmol), diacetoxypalladium (0.092 g, 0.411 mmol) and toluene (30 mL) were combined and stirred at 40° C. for 10 minutes. 7-Iodo-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridine (1.500 g, 4.11 mmol) suspended in toluene (8 mL), 2-(5-chloro-2-fluorophenyl)-5-methylpyrimidin-4-amine (0.976 g, 4.11 mmol) and sodium 2-methylpropan-2-olate (0.592 g, 6.16 mmol) were added. The mixture was sparged with nitrogen and heated at 100° C. overnight. The reaction was then cooled, MeOH (5 mL) was added and the mixture was concentrated directly onto silica gel and purified by chromatography eluted with EtOAc/hexanes step gradient (35-50%) to give N-(2-(5-chloro-2-fluorophenyl)-5-methylpyrimidin-4-yl)-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridin-7-amine and N-(2-(5-chloro-2-fluorophenyl)-5-methylpyrimidin-4-yl)-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridin-7-amine. ESI-MS: m/z 475.3 (M+H).

Provenance & Evidence