Triethylamine → HCID 86662093, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 3-(2-fluoropyridine-3-yl)-3-oxopropanoate (1.42 g, 6.71 mmol) was dissolved in anhydrous acetonitrile (20 mL), treated with triethylamine (0.781 mL, 1.15 equiv) and cooled to 0° C. To the mixture was added the 4-acetamidobenzenesulfonyl azide (1.77 g, 1.1 equiv) and after stirring 0° C. for 1 hour, the mixture was treated with sodium hydroxide (10 mL, 1 N aqueous). The mixture was poured into sodium carbonate (50 mL, aqueous saturated) and water (200 mL) and extracted with ethyl acetate (2×250 mL). The combined organic extracts were washed once with brine (50 mL), dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 70:30; hexanes:ethyl acetate), providing the titled compound as a light yellow oil.

Provenance & Evidence