Application of 13526-66-4, A common heterocyclic compound, 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, molecular formula is C6H3BrClN3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
a) ferf-Butyl 4-(imidazo[1 ,2 ine-1 -carboxylateTo a solution of 1-Boc-4-methylene-piperidine (1.29 g, 6.5 mmol, 2.0 eq) in dry THF (10 mL) under nitrogen was added 9-BBN (0.5M in THF, 16.3 mL, 8.16 mmol, 2.5 eq). The reaction mixture was heated at 75C for 3 h. After cooling, the resulting solution was added to a mixture of 6-chloroimidazo[1 ,2-b]pyridazine (0.5 g, 3.2 mmol), Pd(dppf)CI2 (133 mg, 0.16 mmol, 0.05 eq) and K2C03 (1.35 g, 9.8 mmol, 3.0 eq) in DMF (5 mL) and water (1 mL). The reaction mixture was heated at 75C for 16 h then concentrated in vacuo. The residue was dissolved in EtOAc and washed with water (50 mL) and brine (20 mL). The organics were dried over MgS04 and concentrated in vacuo. Purification by chromatography on silica gel gave a solid (0.406 g, 40%); 1H NMR (400 MHz, DMSO-d6) delta ppm 8.21 (s, 1 H), 8.03 (d, J=9.1 Hz, 1 H), 7.71 (s, 1 H), 7.16 (d, J=9.1 Hz, 1 H), 3.91 (m, 2H), 2.55-2.79 (m, 4H), 1.92 (m, 1 H), 1.52-1.65 (m, 2H), 1.38 (s, 9H), 0.99-1.22 (m, 2H); m/z (ES+APCI)+: 317 [M+H]+.
The synthetic route of 13526-66-4 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; OSBORNE, Simon; CHAPMAN, Timothy; WALLACE, Claire; WO2012/127212; (2012); A1;,
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