Pyridine → HCID 59135753、化合物

HRID 504739ノート

反応式

HRID 504739 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2.[CH3:16][N:17]1[CH:21]=[CH:20][N:19]=[C:18]1[S:22](Cl)(=[O:24])=[O:23].N1C=CC=C[CH:27]=1>>[CH3:27][N:1]([S:22]([C:18]1[N:17]([CH3:16])[CH:21]=[CH:20][N:19]=1)(=[O:24])=[O:23])[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2

参加物

4

反応物 3

HCID 1049PyridineHCID 111381941H-Indole-2-carboxylic acid, 7-amino-, ethyl esterHCID 116583831-Methyl-1H-imidazole-2-sulfonyl chloride

生成物 1

HCID 59135753HCID 59135753、化合物収率 59%

実験手順

To a solution of ethyl 7-amino-1H-indole-2-carboxylate (3 g) in pyridine (30 mL) was added 1-methyl-1H-imidazole-2-sulfonyl chloride (3.6 g) under ice-cooling, and the mixture was stirred for 1 hr. The reaction mixture was concentrated, and the residue was dissolved in ethyl acetate. The solution was washed with water. The ethyl acetate layer was washed with 1N hydrochloric acid, saturated brine and saturated aqueous sodium hydrogencarbonate solution, dried (MgSO4), and concentrated. The obtained residue was dissolved in DMF (30 mL), potassium carbonate (2.1 g) and methyl iodide (2.1 g) were added at room temperature, and the mixture was stirred for 3 hr at room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with 1N hydrochloric acid, saturated brine and saturated aqueous sodium hydrogencarbonate solution, dried (MgSO4), and concentrated. The obtained residue was subjected to silica gel column chromatography to give the title compound (3.0 g, yield 59%) as white crystals from a fraction eluted with ethyl acetate:hexane=50:50. melting point 120° C.

後処理

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed with water
  5. washThe ethyl acetate layer was washed with 1N hydrochloric acid, saturated brine and saturated aqueous sodium hydrogencarbonate solution
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. dissolutionThe obtained residue was dissolved in DMF (30 mL)
  9. additionpotassium carbonate (2.1 g) and methyl iodide (2.1 g) were added at room temperature
  10. stirringthe mixture was stirred for 3 hr at room temperature
  11. additionWater was added to the reaction mixture
  12. extractionthe mixture was extracted with ethyl acetate
  13. washThe ethyl acetate layer was washed with 1N hydrochloric acid, saturated brine and saturated aqueous sodium hydrogencarbonate solution
  14. dry with materialdried (MgSO4)
  15. concentrationconcentrated

出典と根拠

ORDレコード
ord-7c1fb5124dd54df8932382a13e14e775
出典データセット
uspto-grants-2010_08
特許番号
US07777047B2

反応ノート

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