Methyl morpholine oxide → Ethyl 3-formylimidazo[1,2-a]pyridine-2-carboxylate

HRID 2229204Notes

Reaction equation

HRID 2229204 reaction equation
[OH:1][CH2:2][C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][C:4]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13].C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH:2]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][C:4]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:1]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 18466901Ethyl 3-(hydroxymethyl)imidazo[1,2-a]pyridine-2-carboxylate

Product 1

HCID 10704014Ethyl 3-formylimidazo[1,2-a]pyridine-2-carboxylateYield 92%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.2 g (5.45 mmol) of ethyl 3-(hydroxymethyl)-imidazolo[1,2-a]pyridine-2-carboxylate in 50 mL dichloromethane is treated with 1.75 g (15.0 mmol) of N-methylmorpholine N-oxide, 2.5 g powdered 4A molecular sieves and 180 mg (0.5 mmol) tetrapropylammonium perruthenate. The mixture is stirred at room temperature for 2 hr and applied directly to a column of silica. The column is eluted with 10% methanol in dichloromethane to afford 1.09 g (92%) ethyl 3-formyl-imidazolo[1,2-a]pyridine-2-carboxylate.

Workup

  1. washThe column is eluted with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-08fbe67506f54b8b91251ad36c267771
Source dataset
uspto-grants-2002_07
Patent number
US06420365B1

Reaction notes

Loading…