Sodium hydride → 6'-Bromo-1'-(8-chloro-2,3-dimethylquinolin-4-yl)-1',2,2',3,5,6-hexahydrospiro-[pyran-4,3'-pyrrolo[3,2-b]pyridine]

Participants

Reaction Steps

Prepared according to procedure M by using 6′-bromo-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine] (150 mg, 0.56 mmol), 4,8-dichloro-2,3-dimethylquinoline (126 mg, 0.56 mmol) and NaH (48.6 mg, 1.11 mmol, 55% dispersion in oil) in DMF (2.5 mL) while heating the reaction at 60° C. for 14 h. Purification by reverse phase HPLC (10 to 60% acetonitrile in water) gave 6′-bromo-1′-(8-chloro-2,3-dimethylquinolin-4-yl)-1′,2,2′,3,5,6-hexahydrospiro-[pyran-4,3′-pyrrolo[3,2-b]pyridine]. Mass Spectrum (ESI) m/e=458.0 [(M+1) (79Br)] and 460.0 [(M+1) (81Br)].

Provenance & Evidence