Diisopropylamine → HCID 86658477, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium, 2.5 M (44.8 mL, 112 mmol) was added slowly to a solution of diisopropylamine (19.16 mL, 134 mmol) in THF (400 mL) at −78° C. The resulting solution was stirred at 0° C. for 15 minutes before cooling to −78° C. A solution of 5-bromo-2-(6-chloropyridin-3-yloxy)-N,N-diethyl-3-fluorobenzamide (30 g, 74.7 mmol) in THF (400 mL), cooled to −78° C., was added dropwise via cannula under positive pressure. The resulting solution was stirred 3 hours at −78° C. before being quenched with saturated ammonium chloride (200 mL). The reaction mixture was diluted with water (20 mL) and extracted with EtOAc (3×250 mL). The combined organic extracts were washed with saturated aqueous ammonium chloride, water, saturated aqueous sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to provide an off white solid that was triturated with methanol. The derived solid was dried under a stream of nitrogen to provide 7-bromo-3-chloro-9-fluoro-5H-chromeno[2,3-c]pyridin-5-one. MS m/z=330.1 [M+H].

Provenance & Evidence