Lithium Hexamethyldisilazide → HCID 59547921, compound

Participants

Reaction Steps

To 2,6-difluoro-N-1H-pyrazol-3-ylbenzamide (for a preparation see Intermediate 9)(45 mg, 0.20 mmol) in dry THF (3.0 ml) under nitrogen at room temperature was added 1.0 M lithium bis(trimethylsilyl)amide in THF (0.20 ml, 0.20 mmol) dropwise. The solution was stirred for approximately 30 min and then 4-(bromomethyl)-3-(trifluoromethyl)phenyl ether (67 mg, 0.20 mmol) in THF (2 ml) was added. The solution was stirred for 3 h and then left to stand overnight. The solvent was removed under a stream of nitrogen. To the residue was added aqueous sodium bicarbonate and then the residue extracted with chloroform three times. The combined chloroform extracts were filtered through a hydrophobic frit. The filtrate was concentrated in vacuo. The residue was purified on MDAP (Method B). The appropriate fractions were combined and the residue dried under high vacuum to give the title compound as a thick white gum (72.3 mg); LCMS: (System 4) MH+=474, tRET=3.35 min.

Provenance & Evidence