Lithium Hexamethyldisilazide → HCID 59547844, compound

Participants

Reaction Steps

To a solution of 2,6-difluoro-N-1H-pyrazol-3-ylbenzamide (for as preparation see Intermediate 9) (0.790 g, 3.54 mmol) in THF (30 ml) was added 1.0 M lithium bis(trimethylsilyl)amide in THF (3.54 ml, 3.54 mmol). The reaction mixture was stirred for 30 min. To the reaction mixture was added 3-(bromomethyl)-4-chlorophenyl phenylmethyl ether (1.11 g, 3.56 mmol) in THF (10 ml). The reaction was stirred overnight, under nitrogen at ambient temperature. The solvent was evaporated in vacuo. The residue was partitioned between ethyl acetate (100 ml) and water (70 ml). The phases were separated and the organic phase washed with brine (70 ml). The phases were separated and the organic phase was evaporated in vacuo. The sample was loaded in dichloromethane and purified on silica (2×100 g) using 0-100% ethyl acetate-cyclohexane. The appropriate fractions were combined and evaporated in vacuo to give the title compound as an off-white gum (1.03 g);

Provenance & Evidence