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

HRID 509617ノート

反応式

HRID 509617 の反応式
[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

参加物

4

反応物 2

HCID 104392-AminopyridineHCID 107931,3-Dichloroacetone

生成物 1

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

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ff1c686454c14e5095b7da4044227324
出典データセット
uspto-grants-2015_08
特許番号
US09096589B2

反応ノート

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