Triethylamine → Imidazo(1,2-a)pyridine-7-carbonitrile

HRID 341199Notes

Reaction equation

HRID 341199 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([C:10]([NH2:12])=O)=[CH:6][C:5]=12.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([C:10]#[N:12])=[CH:6][C:5]=12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 57497683Imidazo[1,2-a]pyridine-7-carboxamide

Product 1

HCID 55267408Imidazo(1,2-a)pyridine-7-carbonitrileYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Imidazo[1,2-a]pyridine-7-carboxylic acid amide (38 mg, 0.24 mmol) and triethylamine (0.066 ml, 0.47 mmol) in CH2Cl2 (5 ml) was added trifluoroacetic anhydride (0.39, 2.83 mmol) dropwise. The reaction mixture was stirred at room temperature for 2 h before the crude mixture was loaded onto a SCX SPE cartridge, washing with MeOH and eluting with the product with 2M NH3/MeOH. Removal of solvent in vacuo afforded the title compounds (32 mg). MS: [M+H]+ 143.

Workup

  1. washwashing with MeOH
  2. washeluting with the product with 2M NH3/MeOH
  3. customRemoval of solvent in vacuo

Sources & evidence

ORD record
ord-0811ed57fac5465c99e93ef93a071123
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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