Chloroacetaldehyde → 7-Iodoimidazo[1,2-a]pyridine

HRID 1446679Notes

Reaction equation

HRID 1446679 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.Cl[CH2:10][CH:11]=O>C(O)C>[I:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:10]=[CH:11][N:8]=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 226075514-Iodopyridin-2-amine

Product 1

HCID 532499347-Iodoimidazo[1,2-a]pyridineYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
83 °C

Procedure

Combine 4-iodo-pyridin-2-ylamine (4.00 g, 18.18 mmol) and chloroacetaldehyde (2.77 mL, 21.82 mmol) in ethanol (40 mL). Attach a reflux condenser, and heat the mixture to 83° C., stir overnight (15 hours), and cool to room temperature. Filter the resulting solution to yield the product as a tan solid (1.40 g, 32%). MS(ES), m/z 245 (M+1)

Workup

  1. temperaturecool to room temperature
  2. filtrationFilter the resulting solution

Sources & evidence

ORD record
ord-076a4249e2d247c3a9ff489d149b2d22
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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