Thionyl Chloride → 6-Fluoroimidazo[1,2-a]pyridine-2-carbonyl Chloride

HRID 1292757Notes

Reaction equation

HRID 1292757 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([OH:13])=O)[N:10]=2)[CH:7]=1.S(Cl)([Cl:16])=O>C1(C)C=CC=CC=1.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([Cl:16])=[O:13])[N:10]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 24386Thionyl Chloride2×HCID 223975086-Fluoroimidazo[1,2-a]pyridine-2-carboxylic acid

Product 1

HCID 179747796-Fluoroimidazo[1,2-a]pyridine-2-carbonyl Chloride

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 1140TolueneSolvent

Procedure

To a suspension of the product of step (b) (20 g) in toluene (250 ml) and tetrabutylammonium chloride (0.3 g) was added thionyl chloride (40 ml) and the mixture refluxed for 4 hrs. A further aliquot of thionyl chloride-(40 ml) was added and the mixture was refluxed for a further 4 hrs. Solvents were evaporated and the residue was azeotroped with toluene to give the sub-title compound as a solid (20 g). This was used without further purification.

Workup

  1. temperaturethe mixture refluxed for 4 hrs
  2. temperaturethe mixture was refluxed for a further 4 hrs
  3. customSolvents were evaporated
  4. customthe residue was azeotroped with toluene

Sources & evidence

ORD record
ord-bae9120d00ce47ca92a70d9cd1b7c209
Source dataset
uspto-grants-2007_07
Patent number
US07238691B2

Reaction notes

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