HCID 121386246, compound → HCID 119086488, compound

HRID 2202892Notes

Reaction equation

HRID 2202892 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:14])=[C:9]([C:11]([NH2:13])=O)[N:10]=2)[CH:7]=1>O=P(Cl)(Cl)Cl>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:14])=[C:9]([C:11]#[N:13])[N:10]=2)[CH:7]=1

Participants

3

Reactant 1

HCID 121386246HCID 121386246, compound

Product 1

HCID 119086488HCID 119086488, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture of 6-iodo-3-methylimidazo[1,2-a]pyridine-2-carboxamide (600 mg) and POCl3 (40 ml) was heated at reflux for 3 h. The mixture was then cooled to room temperature, and the reaction mixture was concentrated in vacuo. The residue was poured into ice-cold saturated NaHCO3 solution, and extracted with EtOAc. The extract was washed with water and brine, dried over Na2SO4 and concentrated in vacuo to give the title compound (500 mg) as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. additionThe residue was poured into ice-cold saturated NaHCO3 solution
  5. extractionextracted with EtOAc
  6. washThe extract was washed with water and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-290e24af90cf4de6a49f8f735c6785a3
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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