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

HRID 2400353Notes

Reaction equation

HRID 2400353 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-dfa71240677f4239a8ec769af4e5927d
Source dataset
uspto-grants-2014_08
Patent number
US08796244B2

Reaction notes

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