Nitrogen → HCID 86653119, compound

Participants

Reaction Steps

To a stirred solution of N-[(6-bromo-5-methoxypyridin-2-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.150 g, 0.372 mmol, 1 eq.) in 2 ml dry THF “degassed” with N2, was added cyclopropylacetylene (0.073 g, 1.11 mmol, 3 eq.) followed by N-ethyldiisopropylamine (0.191 g, 1.48 mmol, 4 eq.), Copper Iodide (0.010 g, 0.056 mmol, 0.15 eq.) and Tetrakis(triphenylphosphine)palladium (0.042 g, 0.037 mmol, 0.1 eq.). The reaction was microwaved 120° C./normal/fixed hold/pre stir 100 s for 1200 s. The reaction was diluted with EtOAc and filtered through a “celite” plug. The solvent was evaporated and the residue purified by chromatography on silica gel to give N-{[6-(cyclopropylethynyl)-5-methoxypyridin-2-yl]methoxy}-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.083 g, 57% yield) as a yellow viscous oil.

Provenance & Evidence