Sodium Iodide → HCID 67206647, compound

Participants

Reaction Steps

A mixture of 6-chloropyridazine-3-carboxylic acid (2-cyclopropylethyl)amide (0.400 g, 1.77 mmol), 1-Boc-3-aminopyrrolidine (0.400 g, 2.1 mmol), tetrabutylammonium bromide (0.120 g, 0.36 mmol) and 1,8-diazabicyclo[5,4,0]undec-7-ene (1.000 g, 6.00 mmol) in 1,4-dioxane (30 mL) was heated under reflux overnight. A catalytic amount of sodium iodide was added and the heating was continued for 16 hours. The solvent was removed in vacuo and the residue was washed with 1 M citric acid (50 mL) and ethyl ether (50 mL) was added. Ultrasonication of the mixture followed by filtration afforded 3-[6-(2-cyclopropylethyl-carbamoyl)pyridazin-3-ylamino]pyrrolidine-1-carboxylic acid tert-butyl ester as a white solid in 81% yield (0.539 g) which was used for next step reaction without further purification.

Provenance & Evidence