Cesium carbonate → 2-(7-(3'-fluoro-6'-methyl-2,2'-bipyridin-4-ylamino)-2H-pyrazolo[4,3-b]pyridin-2-yl)ethanol

Participants

Reaction Conditions

Reaction Steps

N-(3′-Fluoro-6′-methyl-2,2′-bipyridin-4-yl)-2H-pyrazolo[4,3-b]pyridin-7-amine (21 mg, 0.066 mmol), 2-bromoethanol (8.19 mg, 0.066 mmol) and cesium carbonate (42.7 mg, 0.131 mmol) were combined in DMF (5 mL). The mixture was heated at 120° C. for 30 minutes, then cooled and purified by preparative HPLC using a Phenomenex Gemini Prep 5 μm C18, 75×30 mm column eluting with a gradient of 20-70% 10 mmol NH4HCO3 in 20/80 (v/v) water/acetonitrile in 10 mmol NH4HCO3 in water to afford 2-(7-(3′-fluoro-6′-methyl-2,2′-bipyridin-4-ylamino)-2H-pyrazolo[4,3-b]pyridin-2-yl)ethanol (2.1 mg, 8.79% yield). 2-(7-(3′-Fluoro-6′-methyl-2,2′-bipyridin-4-ylamino)-1H-pyrazolo[4,3-b]pyridin-1-yl)ethanol containing fractions were concentrated and subsequently purified by preparative HPLC using a Sunfire Prep 5 μm C18, 75×30 mm column eluting with a gradient of 5-40% acetonitrile (containing 0.035% TFA) in water (containing 0.05% TFA) to afford the title compound as TFA salts.

Provenance & Evidence