6-Hydroxyquinoline → HCID 58710080, compound

Participants

Reaction Steps

To a stirred suspension of sodium hydride (60% dispersion in mineral oil) (24 mg, 0.6 mmol) in anhydrous DMSO (4 mL) under argon, was added 6-hydroxyquinoline (239 mg, 1.65 mmol). The mixture was allowed to stir at rt for 1 h. To this mixture was added 1-[6-(1-tert-butoxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-4-aza-1-azonia-bicyclo[2.2.2]octane chloride (100 mg, 0.3 mmol) in DMSO (0.3 mL), and the mixture stirred for a further 16 h. TLC analysis showed no starting material so the mixture was neutralised with glacial acetic acid and basified with saturated aqueous sodium bicarbonate solution. The product was extracted in to EtOAc (3×50 mL), the organics dried with MgSO4, filtered and concentrated under reduced pressure. The resulting residue was purified on silica gel by elution with iso-hexane:ethyl acetate to yield the title compound. 1H NMR (DMSO, 400 MHz) 1.4 (9H, s), 2.5 (2H, broad), 3.6 (2H, broad), 4.1 (2H, broad), 6.5 (1H, m), 6.7 (1H, s), 7.6 (1H, m), 7.7 (1H, d), 7.9 (1H, s), 8.1 (1H, d), 8.3 (1H, s), 8.4 (1H, d), 8.9 (1H, s), 12.4 (NH, s). MH+=444.24

Provenance & Evidence