Ethyl 2-chloroacetoacetate → Ethyl 7-methoxy-2-methylimidazo[1,2-a]pyridine-3-carboxylate

HRID 2076240Notes

Reaction equation

HRID 2076240 reaction equation
OC1C=CN2C(C(NC)=O)=C(C)N=C2C=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][N:21]=[C:20]([NH2:24])[CH:19]=1.Cl[CH:26]([C:32](=O)[CH3:33])[C:27]([O:29][CH2:30][CH3:31])=[O:28]>C(O)C>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][N:21]2[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:32]([CH3:33])[N:24]=[C:20]2[CH:19]=1

Participants

5

Reactant 3

HCID 11858Ethyl 2-chloroacetoacetateHCID 108987152-Amino-4-MethoxypyridineHCID 178485487HCID 178485487, compound

Product 1

HCID 53485249Ethyl 7-methoxy-2-methylimidazo[1,2-a]pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Note that 7-hydroxy-N,2-dimethylimidazo[1,2-α]pyridine-3-carboxamide 111-B was obtained by the following procedure. To a solution of 4-methoxypyridin-2-amine (prepared as in Org. Prep. & Proc. Int., 29, 1, 117-122, 1997) 2.8 g, 22.6 mmol in ethanol (100 ml) was added ethyl 2-chloro-3-oxobutanoate (6.2 ml, 45.2 mmol) and the resulting solution heated to reflux for 16 hours under a nitrogen atmosphere. The solvents were removed in-vacuo and the yellow solid was titrated with dichloromethane to extract the crude product. The dichloromethane extracts were concentrated and purified by flash chromatography (eluting with ethyl acetate) to yield ethyl 7-methoxy-2-methylimidazo[1,2-α]pyridine-3-carboxylate, 2 g, 38%, as a yellow solid.

Workup

  1. customwas obtained by the following procedure
  2. temperaturethe resulting solution heated
  3. temperatureto reflux for 16 hours under a nitrogen atmosphere
  4. customThe solvents were removed in-vacuo
  5. extractionto extract the crude product
  6. concentrationThe dichloromethane extracts were concentrated
  7. custompurified by flash chromatography (eluting with ethyl acetate)

Sources & evidence

ORD record
ord-c3ef833701c440b381ea38408143b629
Source dataset
uspto-grants-2011_04
Patent number
US07923457B2

Reaction notes

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