Pyridine → Phenyl N-imidazo[1,2-a]pyridin-8-ylcarbamate

HRID 1255771Notes

Reaction equation

HRID 1255771 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=12.N1C=CC=CC=1.Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19]>CC#N.CCOC(C)=O>[C:21]1([O:20][C:18](=[O:19])[NH:10][C:6]2[C:5]3[N:4]([CH:3]=[CH:2][N:1]=3)[CH:9]=[CH:8][CH:7]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 15413215Imidazo[1,2-a]pyridin-8-amine

Product 1

HCID 58442674Phenyl N-imidazo[1,2-a]pyridin-8-ylcarbamateYield 54.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of imidazo[1,2-a]pyridin-8-ylamine (397 mg, 2.98 mmol) in dry CH3CN (5.0 mL) was added pyridine (282 mg, 3.57 mmol) and phenyl chloroformate (467 mg, 2.98 mmol) and the reaction mixture was stirred at rt. After 4 h, the mixture was diluted with EtOAc (100 mL) and washed with saturated aqueous NaHCO3 (50 mL). The organic layer was dried (MgSO4) and concentrated. The residue was purified (FCC) to give imidazo[1,2-a]pyridin-8-yl-carbamic acid phenyl ester (409.1 mg, 54%). MS (ESI+): calcd for C14H11N3O2 m/z 253.09. found 254.1 (M+H)+.

Workup

  1. washwashed with saturated aqueous NaHCO3 (50 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was purified (FCC)

Sources & evidence

ORD record
ord-8c9c36a9b0644d3f9db6f91464d895c6
Source dataset
uspto-grants-2013_06
Patent number
US08461159B2

Reaction notes

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