Lithium hexamethyldisilazane → HCID 59547928, compound

2,6-difluoro-N-1H-pyrazol-3-ylbenzamide (for a preparation see Intermediate 9)(45 mg, 0.202 mmol) in dry THF (3.0 ml) was stirred under nitrogen at ambient temperature, 1.0 M lithium bis(trimethylsilyl)amide (0.20 ml, 0.20 mmol) was added dropwise and the solution stirred for approximately 90 min then 1-bromo-2-(bromomethyl)-3-[(trifluoromethyl)oxy]benzene (67.3 mg, 1 equiv) in THF (2 ml) was added. The solution was stirred for 5 h then left to stand overnight. The solvent was removed using a stream of nitrogen. To the residue was added aqueous sodium bicarbonate and the mixture was extracted with chloroform three times. The combined organic extracts were filtered through a hydrophobic frit and the filtrate was concentrated in vacuo. The residue was purified by MDAP (Method B). The appropriate fractions were combined and evaporated in vacuo to give the title compound as a white solid (80.6 mg) after drying at high vacuum at 45° C.; LCMS: (System 4) MH+=476, tRET=3.01 min.