3-Bromo-6-chloroimidazo(1,2-b)pyridazine → (6-Chloroimidazo[1,2-b]pyridazin-3-yl)(7-fluoroquinolin-6-yl)methanol

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Reaction Conditions

Reaction Steps

3-Bromo-6-chloro-imidazo[1,2-b]pyridazine (CAS 13526-66-4, 1.327 g, 5.71 mmol) was dissolved THF (40 mL) and under nitrogen conditions, it was cooled down to 0° C. and ethylmagnesium bromide solution (1 M, 6.85 mL) was added. The RM was stirred at RT for 30 min then a solution of 7-fluoro-quinoline-6-carbaldehyde (Intermediate K, 1.0 g, 5.71 mmol) in THF (20 mL) was added by 0° C. The RM was stirred at RT for 2 h. The solvent was partially removed by evaporation and water (40 mL) was added to the residual mash. After 1 h stirring, the crystallized product was filtered and dried overnight under vacuum to afford the title compound as a powder (tR 3.70 min (conditions 5), MH+=329, 1H-NMR in DMSO-d6: 8.90 (dd, 1H); 8.46 (d, 1H); 8.29-8.23 (m, 2H); 7.72 (d, 1H); 7.54-7.49 (m, 2H); 7.40 (d, 1H); 6.56-6.49 (m, 2H)).

Provenance & Evidence