Potassium Fluoride → Methyl 1-[2-(4-tert-butoxyphenoxy)ethyl]-4-(3-ethoxyphenyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylate

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Reaction Steps

Methyl 1-[2-(4-tert-butoxyphenoxy)ethyl]-4-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate (1 g, 2.482 mmole), 3-ethoxyphenylboronic acid (0.618 g, 3.72 mmole), KF (0.433 g, 7.45 mmole), and bis(tri-t-butylphosphine)palladium(0) (0.127 g, 0.248 mmole) were combined in 1,4-dioxane (10 mL). The mixture was degassed (3× pump/N2) then heated to reflux. After 5 hr the mixture was cooled to RT, diluted with EtOAc, filtered through a pad of Celite washing with EtOAc, and concentrated. Flash column chromatography (Biotage-SNAP-50 g SiO2, 0-30% EtOAc/hexanes) gave the title compound (939 mg, 77%) as an off-white foam. 1H NMR (400 MHz, CDCl3): 8.52 (d, J=6.0 Hz, 1 H); 7.61 (d, J=0.9 Hz, 1 H); 7.52-7.47 (m, 2 H); 7.43 (d, J=7.2 Hz, 2

Provenance & Evidence