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ChemicalBook CAS DataBase List Imidazo[1,2-a]pyridine-2-carboxaldehyde, 6-methyl- (9CI)
202348-55-8

Imidazo[1,2-a]pyridine-2-carboxaldehyde, 6-methyl- (9CI) synthesis

1synthesis methods
-

Yield:-

Reaction Conditions:

with manganese(IV) oxide in dichloromethane at 20; for 92.5 h;Heating / reflux;

Steps:

334.c

Step (c) 6-Methylimidazo[l,2-a]pyridine-2-carbaldehydeTo a solution of (6-methylimidazo[l,2-a]pyridin-2-yl)methanol (0.84 g, 5.18 mmol) in DCM (15 ml) was added manganese dioxide (0.450 g, 5.18 mmol) and the reaction mixture was stirred under nitrogen at ambient temperature for 1.5 h and left to stand for a further 18 h. The reaction mixture was heated to reflux for 3 h before further manganese dioxide (2.5 g, 28.76 mmol) and DCM (15.00 ml) was added. The reaction mixture was stirred at reflux for 3 Ii and left to stand at room temperature for 67 h. The mixture was filtered through a pad of celite, washing with DCM. The filtrate was concentrated, triturated with ether and filtered to give the sub title compound as a beige solid (0.283 g). 1H NMR (400 MHz, CDCl3) δ 10.13 (s, IH), 8.07 (s, IH), 7.94 (d, J = 1.3 Hz, IH), 7.58 (d, J = 9.5 Hz, IH), 7.14 (dd, J = 9.5, 1.5 Hz, IH), 2.38 (s, 3H). [M+H]=161

References:

WO2008/84223,2008,A2 Location in patent:Page/Page column 424-425

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