2-Aminopyridine → 2-Chloromethyl-imidazo(1,2-A)pyridine

HRID 509617Notes

Reaction equation

HRID 509617 reaction equation
[Cl:1][CH2:2][C:3](=O)[CH2:4]Cl.[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1>COCCOC>[Cl:1][CH2:2][C:3]1[N:7]=[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]2[CH:4]=1

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 107931,3-Dichloroacetone

Product 1

HCID 9576142-Chloromethyl-imidazo(1,2-A)pyridine

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

The method of Vanelle et al. Tetrahedron 1991, 47, 5173-5184 was used. To a solution of 1,3-dichloro-2-propanone (2.69 g, 21.2 mmol) in 1,2-dimethoxyethane (5 mL) was added 2-aminopyridine and the mixture was stirred at room temperature for 2 hours. During this time a thick precipitate formed, and this was collected by filtration. The precipitate was refluxed in absolute ethanol for 2 hours after which volatiles were removed by evaporation. The residue was dissolved in water (30 mL) and solid NaHCO3 was added to neutralize the mixture. A white precipitate formed, and this was collected by filtration, washed with water and vacuum dried to yield the title compound pure as a cream white solid (1.43 g, 42%). 1H NMR (500 MHz, CDCl3): δ8.08 (d, J=6.7 Hz, 1H), 7.62 (s, 1H), 7.58 (d, J=9.0 Hz, 1H), 7.17-7.22 (m, 1H), 6.80 (t, J=6.8 Hz, 1H), 4.78 (s, 2H).

Workup

  1. customDuring this time a thick precipitate formed
  2. filtrationthis was collected by filtration
  3. temperatureThe precipitate was refluxed in absolute ethanol for 2 hours after which volatiles
  4. customwere removed by evaporation
  5. dissolutionThe residue was dissolved in water (30 mL)
  6. additionsolid NaHCO3 was added
  7. customA white precipitate formed
  8. filtrationthis was collected by filtration
  9. washwashed with water and vacuum
  10. customdried

Sources & evidence

ORD record
ord-ff1c686454c14e5095b7da4044227324
Source dataset
uspto-grants-2015_08
Patent number
US09096589B2

Reaction notes

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