(3-Fluoropyridin-2-yl)methanol → HCID 67280261, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-3-(2-fluoro-phenyl)-5-(4,4,5,5-tetramethyl[1,3,2]-dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (100 mg, 0.2 mmol), 5-bromo-pyridin-3-yl)-(3-fluoro-pyridin-2-yl)-methanol (57 mg, 0.2 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (7 mg, 0.01 mmol) in THF/Acetonitrile/saturated NaHCO3 (5 ml/5 ml/5 ml) was stirred at 120° C. in the microwave for 20 minutes. The mixture was allowed to cool down to room temperature and then extracted with ethyl acetate (2×). The combined organic layers were extracted with brine, dried with Na2SO4, decanted, and concentrated to dryness. Silica chromatography of the crude using a gradient of ethyl acetate and hexane afforded {5-[4-chloro-3-(fluoro-phenyl)-1-(2-trimethylsilanyl-ethoxy-methyl)-1H-pyrrolo[2,3-b]pyridine-5-yl]-pyridin-3-yl}-(3-fluoro-pyridin-2-yl)-methanol (102 mg, 88% yield).

Provenance & Evidence