Ethyl 2-chloroacetoacetate → Ethyl 8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate

HRID 2275757Notes

Reaction equation

HRID 2275757 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[C:10]([NH2:15])=[N:11][CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH:17]([C:23]([CH3:25])=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(O)C>[CH:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:23]([CH3:25])[N:15]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 138258903-(Cyclohexylmethoxy)pyridin-2-amine

Product 1

HCID 14676222Ethyl 8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

130 g of 3-(cyclohexylmethoxy)pyridine-2-amine (Example 4A; 630 mmol, 1 equivalent) were initially charged in 3950 ml of ethanol, and 436 ml of ethyl 2-chloroacetoacetate (3.2 mol, 5 equivalents) were added. The mixture was heated under reflux for 24 h and then concentrated under reduced pressure. The crude product obtained in this manner was chromatographed on silica gel using cyclohexane/diethyl ether as mobile phase, giving 66.2 g (33% of theory) of the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 24 h
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product obtained in this manner
  5. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-9cf2308cedcb4c64971b2f5fed17c2e0
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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