Lithium Hexamethyldisilazide → HCID 178522169, compound

Participants

Reaction Steps

To a stirred solution of 5-chloro-2-(1-cyclohexylmethyl-5,6-difluoro-1H-benzoimidazol-2-yl)-phenylamine (60 mg, 0.16 mmol) in dry tetrahydrofuran (15 ml) was added lithium bis(trimethylsilyl)amide at −30° C. and stirring continued for 30 minutes at that temperature. To this was added a solution of 2-fluoro-4-(1H-tetrazol-5-yl)-benzoic acid methyl ester (42 mg, 0.19 mmol) in tetrahydrofuran (5 ml) at −30° C. The temperature was then allowed to slowly rise to 25° C., and the reaction mixture was allowed to stir for 13 h. The reaction mixture was quenched with saturated aqueous solution of ammonium chloride, extracted with ethyl acetate (3×5 ml). Combined organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography over silica gel (ethyl acetate to 4% methanol/ethyl acetate) gave the desired final compound as light yellow powder (30%). MS (Turbo Spray): m/z=566.4 (M+H).

Provenance & Evidence