1,4-Dioxane → HCID 178501948, compound

Participants

Reaction Conditions

Reaction Steps

The mixture of 5-[2-bromo-4-(2,4-dichlorophenyl)-1,3-thiazol-5-yl]-4H-1,2,4-triazol-3-amine (0.0300 g, 0.0767 mmol), methyl [4-(trimethylstannyl)pyridin-2-yl]carbamate (0.0362 g, 0.115 mmol), Lithium chloride (9.76 mg, 0.230 mmol), Copper(I) iodide (7.0 mg, 0.037 mmol) and Tetrakis(triphenylphosphine)palladium(0) (7.0 mg, 0.0060 mmol) in dry 1,4-Dioxane (4.0 mL, 51 mmol) was purged with N2 for 5 min, heated to reflux (120° C.) under N2 atmosphere for 3 hours, cooled to r.t. . . . . The mixture was diluted with 10% MeOH-DCM (10 mL), filtered through a short column of Celite/Na2SO4. The filtrate was rotavaped and the residue was chromatographed in a 8 g AnaLogix column using MeOH/DCM (0/100 to 5/95) to give a solid product (0.0084 g, 24% yield). LCMS: (FA) ES+ 462, 464, ES− 460, 462. 1H NMR (400 MHz, d-chloroform & d4-Methanol) 8.21 (s, 1H), 8.05 (s, 1H), 7.30-7.32 (m, 1H), 7.19-7.24 (m, 2H), 7.06-7.09 (m, 1H), 3.54 (s, 3H).

Provenance & Evidence