Dichloromethane → HCID 20072898, compound

HRID 704623Notes

Reaction equation

HRID 704623 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]2[CH:10]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[N:12]=[C:6]2[CH:5]=1)(=O)[NH2:2].C(Cl)Cl.FC(F)(F)C(OC(=O)C(F)(F)F)=O>N1C=CC=CC=1>[C:1]([C:4]1[CH:9]=[CH:8][N:7]2[CH:10]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[N:12]=[C:6]2[CH:5]=1)#[N:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 9845Trifluoroacetic anhydrideHCID 20072840HCID 20072840, compound

Product 1

HCID 20072898HCID 20072898, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a suspension of methyl 7-carbamoylimidazo[1,2-a]-pyridine-2-carboxylate (1.5 g), methylene chloride (30 ml) and pyridine (2.7 g) was dropwise added trifluoroacetic anhydride (3.6 g) over the period of 5 minutes under cooling with stirring, and the mixture was stirred for 30 minutes at the same temperature. The reaction mixture was poured into ice water (30 ml) and extracted with 5% solution of methanol in chloroform. The organic layer was dried over magnesium sulfate and concentrated. The residue was subjected to a column chromatography on silica gel (50 g) and eluted with 20% solution of methanol in chloroform. The fractions containing the object compound were combined and concentrated to give methyl 7-cyanoimidazo[1,2-a]pyridine-2-carboxylate (0.4 g).

Workup

  1. customover the period of 5 minutes
  2. temperatureunder cooling
  3. stirringthe mixture was stirred for 30 minutes at the same temperature
  4. extractionextracted with 5% solution of methanol in chloroform
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated
  7. washeluted with 20% solution of methanol in chloroform
  8. additionThe fractions containing the object compound
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c9148af8aeb84fa686a6b7f192119cac
Source dataset
uspto-grants-1991_01
Patent number
US04988698

Reaction notes

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