N-bromobutanimide → 5'-Bromo-1'-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-6'-(4-morpholinyl)-1',2,2',3,5,6-hexahydrospiro[pyran-4,3'-pyrrolo[3,2-b]pyridine]

Participants

Reaction Steps

To a stirred solution of 1′-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-6′-(4-morpholinyl)-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine] (250 mg, 0.489 mmol) in acetonitrile (6 mL) at 0° C. was added dropwise via syringe over 5 min a solution of N-bromosuccinimide (87 mg, 0.489 mmol) in acetonitrile (4 mL). The reaction was stirred at this temperature for 15 min. After this time the reaction was partitioned between EtOAc (40 mL) and water (15 mL). The separated organic layer was washed with NaHCO3 (15 mL, saturated aqueous solution) and Na2S2O3 (15 mL, saturated aqueous solution) and then it was dried over MgSO4, filtered and evaporated in vacuo to give 5′-bromo-1′-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-6′-(4-morpholinyl)-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine]. 1H NMR (400 MHz, chloroform-d) δ ppm 8.74 (1H, dt, J=4.8, 1.4 Hz), 7.83-7.99 (3H, m), 7.70 (1H, dd, J=9.2, 5.9 Hz), 7.42 (1H, ddd, J=6.8, 4.7, 2.2 Hz), 7.28-7.34 (1H, m), 5.97 (1H, s), 4.10-4.20 (2H, m), 3.94-4.06 (2H, m), 3.74-3.84 (4H, m), 3.49-3.64 (2H, m), 2.78-2.94 (4H, m), 2.28-2.46 (5H, m), 1.72-1.88 (2H, m). Mass Spectrum (ESI) m/e=590.0 [(M+1) (79Br)] and 592.0 [(M+1) (81Br)]

Provenance & Evidence