Lithium Hexamethyldisilazide → HCID 59547999, compound

Participants

Reaction Steps

To a stirred solution of 1H-1,2,3-triazole (34 mg, 0.492 mmol, Alfa Aesar) in THF (2 ml) at ambient temperature under nitrogen was added 1.0 M lithium bis(trimethylsilyl)amide in THF (0.5 ml, 0.500 mmol). The resulting yellow cloudy mixture was stirred at ambient temperature for 10 min. To a solution of N-(1-{[4-(bromomethyl)-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)-2,6-difluorobenzamide (for a preparation see Intermediate 22)(49 mg, 0.103 mmol) in THF (2 ml) at ambient temperature was added a solution of the 1H-1,2,3-triazole anion (0.5 ml, 0.167 mmol). After 1.5 h, a further amount of 1H-1,2,3-triazole anion (0.5 ml, 0.167 mmol) was added to the mixture and stirred overnight. The solvent was removed in vacuo and the residue was dissolved in 1:1 MeOH:DMSO (1 ml) and purified by MDAP on Sunfire C18 column using Acetonitrile-Water with a Formic acid modifier (Method B). The solvent was evaporated in vacuo to give the title compound as a colourless gum (1.8 mg); LCMS: (System 4) MH+=463.1, tRET=2.85 min.

Provenance & Evidence