Lithium Hexamethyldisilazide → HCID 59547898, compound

Participants

Reaction Steps

To a stirred solution of 2,6-difluoro-N-1H-pyrazol-3-ylbenzamide (for a preparation see Intermediate 9)(0.05 g, 0.224 mmol) in dry THF (1.5 ml) under nitrogen was added a 1 M solution of lithium bis(trimethylsilyl)amide in THF (0.224 ml, 0.224 mmol, Aldrich) dropwise, fairly quickly. The solution was stirred for 30 min then a solution of 2-(bromomethyl)-3-chlorophenyl methyl ether (for a preparation see Intermediate 25)(0.053 g, 0.224 mmol) in dry THF (1.5 ml) was added and stirring continued for 90 min then the solution was left to stand overnight. The solvent was removed in vacuo and the residue was partitioned between chloroform and half saturated sodium bicarbonate and the aqueous phase further extracted with chloroform, the chloroform fractions being filtered through a phase separator. The chloroform was removed in vacuo and the residue purified on MDAP (Method B) to give the title compound as a white solid (0.07 g); LCMS: (System 4) MH+=378, tRET=2.77 min.

Provenance & Evidence