Propargyl alcohol → HCID 10271274, compound

Participants

Reaction Steps

Under an argon atmosphere, a mixture of N-(4-chlorobenzyl)-6-iodo-1-methyl4-oxo-1,4-dihydropyrido[2,3-c]pyridazine-3-carboxamide (Preparation 23, 0.053 g), dichlorobis(triphenylphosphine)palladium (II) (4.1 mg), copper(I) iodide (18.3 mg), and diethylamine (1.5 mL) is treated with a solution of propargyl alcohol (11 μL). The reaction mixture is stirred at room temperature overnight. The mixture is diluted with EtOAc and then filtered through a Celite-packed, sintered-glass funnel. The cake is washed with CHCl3 until the washings are colorless. The organic filtrate is washed with aqueous saturated ammonium chloride and water, dried (Na2SO4) and concentrated in vacuo. The crude solid is triturated with ether, filtered and washed with ether to give 0.032 g (71%) of the title compound as a light brown solid. Physical characteristics: mp 201-206° C.; 1H NMR (400 MHz, DMSO-d6) δ 4.21, 4.39, 4.54, 5.51, 7.40, 8.52, 9.0, 9.7; IR (drift) 3368, 1660, 1612, 1597, 1551, 1479, 1410, 1397, 1377, 1353, 1256, 1036, 812, 674, 650 cm−1; MS (EI) m/z 382 (M+, 6); HRMS (FAB) m/z 383.0917 (C19H15ClN4O3+H).

Provenance & Evidence