Triethyloxonium tetrafluoroborate → [1-(6-Fluoro-1-pyridin-4-yl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester

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Reaction Steps

To a suspension of (S)-Boc-alaninamide (385 mg, 2.05 mmol) in DCM (5 mL) was added triethyloxonium tetrafluoroborate (389 mg, 2.05 mmol) in one portion under a nitrogen atmosphere. The resulting mixture was left to stir at RT for 1 h. The volatiles were removed under reduced pressure and to the resulting residue was added 4-fluoro-N2-pyridin-4-yl-benzene-1,2-diamine (208 mg, 1.02 mmol) in absolute EtOH (5 mL) and the mixture was stirred at 80° C. for 16 h. The volatiles were removed under reduced pressure and the resulting residue partitioned between DCM and a saturated aqueous solution of NaHCO3. The organic fraction was dried, concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, gradient 0-10% MeOH in EtOAc) to afford the title compound as a pale yellow oil (210 mg, 58%). LCMS (Method C): RT 2.84 min [M+H]+ 357.15

Provenance & Evidence