1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → N-(3'-fluoro-6'-methyl-2,2'-bipyridin-4-yl)-1-isopropyl-1H-pyrazolo[4,3-b]pyridin-7-amine

Participants

Reaction Conditions

Reaction Steps

7-Iodo-1-isopropyl-1H-pyrazolo[4,3-b]pyridine (24 mg, 0.084 mmol), Tris(dibenzylideneacetone)dipalladium(0) (2.82 mg, 3.08 μmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (17.80 mg, 0.031 mmol), 3′-fluoro-6′-methyl-2,2′-bipyridin-4-amine (25 mg, 0.123 mmol) and sodium 2-methylpropan-2-olate (35.5 mg, 0.369 mmol) were combined in dioxane (5 mL). The mixture was heated at 120° C. for 2 hours, then cooled and purified by preparative HPLC using a Phenomenex Gemini Prep 5 μm C18, 75×30 mm column eluting with a gradient of 20-50% 10 mmol NH4HCO3 in 20/80 (v/v) water/acetonitrile in 10 mmol NH4HCO3 in water to afford N-(3′-fluoro-6′-methyl-2,2′-bipyridin-4-yl)-1-isopropyl-1H-pyrazolo[4,3-b]pyridin-7-amine (7 mg, 15.70% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.48 (s, 6H) 2.61 (s, 3H) 5.08-5.21 (m, 1H) 7.03 (dd, J=5.81, 2.02 Hz, 1H) 7.36-7.47 (m, 2H) 7.49 (s, 1H) 7.62-7.71 (m, 1H) 8.30 (s, 1H) 8.42 (d, J=6.06 Hz, 1H) 8.51 (d, J=4.80 Hz, 1H). MS [M+H] found 363.4.

Provenance & Evidence