Sodium Carbonate → 4-[(5-Chloro-6-isopropoxypyridin-3-yl)oxy]-3-(2-methoxypyridin-3-yl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-bromo-4-[(5-chloro-6-isopropoxypyridin-3-yl)oxy]benzonitrile (Preparation 25, 638 mg, 1.74 mmol) and 2-methoxy-3-pyridylboronic acid (265 mg, 1.74 mmol) in dioxan (10.5 mL) was added a 1 M aqueous solution of sodium carbonate (5.2 mL, 5.21 mmol). The reaction was sparged with nitrogen before the addition of tetrakis(triphenylphosphine)palladium(0) (200 mg, 0.17 mmol). The reaction mixture was heated to 100° C. and stirred for 16 hours and then concentrated in vacuo The residue was partitioned between water (30 mL) and EtOAc (25 mL). The aqueous phase was separated and extracted with EtOAc (2×25 mL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford a yellow oil which was purified by silica gel column chromatography, eluting with 9:1 heptane/EtOAc. Fractions containing product were combined and concentrated in vacuo to obtain the title compound as a colourless oil (534 mg, 60%).

Provenance & Evidence