Ethyl diazoacetate → Ethyl 2-(6-iodo-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxylate

HRID 2202995Notes

Reaction equation

HRID 2202995 reaction equation
[CH:1]([C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][C:8]([I:11])=[CH:7][N:6]2[C:12]=1[CH3:13])=[CH2:2].[N+](=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N-]>C1(C)C(C)=CC=CC=1>[I:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:12]([CH3:13])=[C:3]([CH:1]3[CH2:2][CH:16]3[C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:4]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 12192Ethyl diazoacetateHCID 89690289HCID 89690289, compound

Product 1

HCID 121386225Ethyl 2-(6-iodo-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a stirred solution of 2-ethenyl-6-iodo-3-methylimidazo[1,2-a]pyridine (680 mg) in xylene (20 ml) was added ethyl diazoacetate (1.5 ml) at room temperature. The reaction mixture was heated at reflux for 5 h. The resulting reaction mixture was then cooled to room temperature, concentrated in vacuo, and purified by preparative HPLC to afford the title compound (200 mg) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 5 h
  3. customThe resulting reaction mixture
  4. concentrationconcentrated in vacuo
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-5ccadf76d9774c02b8e1aeb136a7d9e7
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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