Dimethylformamide → HCID 117737016, compound

Participants

Reaction Conditions

Reaction Steps

A RBF was charged with 1-(5,6-dichloro-2-methoxypyridin-3-yl)-2-oxo-N-(pyridazin-3-yl)-1,2-dihydroquinoline-6-sulfonamide (0.075 g, 0.157 mmol), ethynylcyclopentane (0.074 ml, 0.784 mmol), diisopropylamine (0.134 ml, 0.941 mmol), copper(i) iodide (2.66 μl, 0.078 mmol), tetrakis(triphenylphosphine)palladium(0) (0.018 g, 0.016 mmol), and DMF (0.784 ml). The reaction was stirred at 100° C. for 18 hrs. The mixture was diluted with water and Ethyl Acetate. The organic portion was collected, dried with sodium sulfate, filtered, and concentrated. The crude material was purified via column chromatography (RediSep Gold 40 g, gradient elution 10-75% [3:1 EtOAc/EtOH]:Heptane to give 1-(5-chloro-6-(cyclopentylethynyl)-2-methoxy-3-pyridinyl)-2-oxo-N-3-pyridazinyl-1,2-dihydro-6-quinolinesulfonamide (55 mg, 0.103 mmol, 65.4% yield) as an off-white solid. m/z (ESI) 536.0 (M+H)+.

Provenance & Evidence