Phosphorus Pentoxide-Methanesulfonic Acid → 5-imidazol-1-yl-1H-indole-2-carboxylic acid ethyl ester

HRID 74461ノート

反応式

HRID 74461 の反応式
[CH2:1]([O:3][C:4](=[O:19])/[C:5](=[N:7]/[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)=[CH:10][CH:9]=1)/[CH3:6])[CH3:2].CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[CH2:1]([O:3][C:4]([C:5]1[NH:7][C:8]2[C:9]([CH:6]=1)=[CH:10][C:11]([N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1)=[CH:12][CH:13]=2)=[O:19])[CH3:2]

参加物

4

反応物 2

HCID 86584057Phosphorus Pentoxide-Methanesulfonic AcidHCID 178471939HCID 178471939、化合物

生成物 1

HCID 513623175-imidazol-1-yl-1H-indole-2-carboxylic acid ethyl ester

試薬・触媒・溶媒 1

HCID 62657Potassium Phosphate, Tribasic溶媒

反応条件

温度
100 °C

実験手順

2-[(E)-4-Imidazol-1-yl-phenylimino]-propionic acid ethyl ester (842 mg) was added to an Eaton's reagent (4 ml), and this was stirred at 100° C. for one hour. After adjusting the pH of the reaction mixture to 11 using an aqueous solution (about 10 ml) of 20% potassium phosphate, the mixture was extracted with ethyl acetate (30 ml). The organic layer was washed with an aqueous solution saturated with sodium chloride (20 ml), and the organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane/methanol). Thus, 5-imidazol-1-yl-1H-indole-2-carboxylic acid ethyl ester was obtained as a yellow amorphous material (370 mg, 47%).

後処理

  1. extractionthe mixture was extracted with ethyl acetate (30 ml)
  2. washThe organic layer was washed with an aqueous solution saturated with sodium chloride (20 ml)
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (dichloromethane/methanol)

出典と根拠

ORDレコード
ord-fb7583543c5e4ae7b1af14d67f34695d
出典データセット
uspto-grants-2014_09
特許番号
US08829199B2

反応ノート

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