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ChemicalBook CAS DataBase List 3-Boc-7-chloro-3H-imidazo[4,5-b]pyridine
878011-41-7

3-Boc-7-chloro-3H-imidazo[4,5-b]pyridine synthesis

3synthesis methods
-

Yield:878011-41-7 76%

Reaction Conditions:

with dmap in dichloromethane at 20; for 0.5 h;

Steps:

2

To a solution of 6-chloro-1-deazapurine (10 g, 65.1 mmol, J. Heterocyclic Chem. 1982, 19, 513-517) and BOC2O (19.8 g, 91.2 mmol) in dry dichloromethane (100 ml) was added dimethylaminopyridine (0.5 g, 5 mass %) and the mixture was stirred at room temperature for 30 minutes. The reaction was quenched by adding silica and the mixture was filtered over hyflo. Evaporating the solvent yielded the crude product. Trituration with petroleum ether followed by treatment with ether yielded the product as a white solid (6.29 g, 76%), mp: 183.5° C. decomposition 1H NMR (d6-DMSO) δ 8.89 (s, 1H, H-8), 8.47-8.46 (d, J 5.3 , 1H, H-2), 7.62-7.61 (1H, d, J 5.3, H-1), 1.66 ( s, 9H t-Bu).

References:

US2006/52412,2006,A1 Location in patent:Page/Page column 4