Potassium Carbonate → 4-Chloro-1-(5-ethoxycarbonylpyrid-2-yl)-2-methylimidazo[4,5-c]pyridine

HRID 1085144ノート

反応式

HRID 1085144 の反応式
[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1.Cl[C:13]1[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[N:10]([C:13]3[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][N:14]=3)[C:6]=2[CH:5]=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 2799611Ethyl 6-chloronicotinateHCID 198771904-Chloro-2-methyl-3H-imidazo[4,5-c]pyridine

生成物 1

HCID 198771824-Chloro-1-(5-ethoxycarbonylpyrid-2-yl)-2-methylimidazo[4,5-c]pyridine収率 51%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-Chloro-2-methylimidazo[4,5-c]pyridine* (3.34 g, 20 mmol), and ethyl 6-chloronicotinate (3.71 g, 26.2 mmol) were dissolved in N,N-dimethylformamide (42 ml). Potassium carbonate (2.76 g, 20 mmol) was added and the mixture was refluxed overnight. The reaction mixture was cooled, the solvent removed under reduced pressure and the crude product purified by flash chromatography eluting with ethyl acetate. Fractions containing product were evaporated and the resulting foam triturated with ether. The solid was filtered and dried under reduced pressure yielding the title compound as a yellow solid (3.2 g, 51%).

後処理

  1. temperaturethe mixture was refluxed overnight
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent removed under reduced pressure
  4. customthe crude product purified by flash chromatography
  5. washeluting with ethyl acetate
  6. additionFractions containing product
  7. customwere evaporated
  8. customthe resulting foam triturated with ether
  9. filtrationThe solid was filtered
  10. customdried under reduced pressure

出典と根拠

ORDレコード
ord-b5a1b38c357b4ec79d5699f9d65c71c1
出典データセット
uspto-grants-1991_04
特許番号
US05008263

反応ノート

読み込み中…