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ChemicalBook CAS DataBase List 6-CHLORO-IMIDAZO[1,2-A]PYRIDINE-2-CARBALDEHYDE
881841-30-1

6-CHLORO-IMIDAZO[1,2-A]PYRIDINE-2-CARBALDEHYDE synthesis

3synthesis methods
-

Yield:-

Reaction Conditions:

with manganese(IV) oxide in dichloromethane; for 0.5 h;Heating / reflux;

Steps:

8.a

Step (a) 6-chloroimidazo[l,2-a]pyridine-2-carbaldehyde; 6-Chloro-imidazo[l,2-a]pyridine-2-carboxylic acid (0.4 g, 2 mmol) was dissolved in dry THF (10 ml) and 1.0M borane/THF solution (5 ml, 5 mmol) was added, and the mixture heated at reflux for 2h. Mixture was quenched with methanol (2 ml), acidified with 3 drops of concentrated hydrochloric acid and heated at reflux for 15 min. The mixture was then adsorbed on to SCX resin, washed well with methanol and the crude alcohol intermediate eluted with 10% aqueous ammonia in methanol. This intermediate (0.4 g, 2.2 mmol) was mixed with manganese dioxide (2 g, 23 mmol) in dichloromethane (50 ml) and was heated at reflux for 30 min. The inorganics were removed by filtration and the filtrate evaporated to dryness to afford the sub-title compound (0.32 g, 89%). 1H NMR (300 MHz, CDCl3): δ 10.22 (s, IH), 8.33 (s, IH), 8.09 (s, IH), 7.64 (d, IH), 7.27 (dd, IH)

References:

WO2008/84236,2008,A1 Location in patent:Page/Page column 40-41

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