HCID 67383577, compound → HCID 67383508, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 2-(4-bromo-2-iodophenoxy)-6-fluoro-5-(trimethylsilyl)nicotinate (2.04 g, 3.89 mmol) was dissolved in dry THF (80 mL) and cooled in a dry ice bath to −78° C. Isopropylmagnesium chloride (2.0 M solution in diethyl ether, 3.89 mL (7.78 mmol) was added and the solution stirred for 15 minutes. The mixture was removed from the cold bath and allowed to slowly warm to RT. Water (100 mL), saturated ammonium chloride (10 mL), and EtOAc (200 mL) were added and the phases mixed and separated. The organics were dried with magnesium sulfate and evaporated to dryness under reduced pressure. The crude was purified using silica chromatography (hexane to ethyl acetate gradient) to give 7-bromo-2-fluoro-3-(trimethylsilyl)-5H-chromeno[2,3-b]pyridin-5-one.

Provenance & Evidence