Nitrogen → N-{1-[2-(cyclopropylethynyl)-1,3-thiazol-4-yl]ethoxy}-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

Participants

Reaction Steps

To a stirred solution of N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.15 g, 0.38 mmol, 1 eq.) in 2 ml dry THF “degassed” with N2, was added Cyclopropylacetylene (70%, 0.144 g, 1.52 mmol, 4 eq.) followed by N-ethyldiisopropylamine (0.256 g, 1.98 mmol, 5.2 eq.), Copper Iodide (0.022 g, 0.1141 mmol, 0.3 eq.) and Tetrakis(triphenylphosphine)palladium (0.132 g, 0.114 mmol, 0.2 eq.). The reaction was microwaved 120° C./normal/fixed hold/pre stir 100 s for 180 s. The reaction was diluted with EtOAc and filtered through a “celite” plug. The solvent was evaporated and the residue was purified by chromatography on silica gel to give N-{1-[2-(cyclopropylethynyl)-1,3-thiazol-4-yl]ethoxy}-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.074 g, 48% yield) as a yellow viscous oil.

Provenance & Evidence