Potassium Iodide → 5-(1-Ethoxycarbonyl-1-methyl-ethoxy)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester

HRID 966499

反応式

HRID 966499 の反応式
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[CH:8][C:7]([OH:21])=[CH:6][CH:5]=2.[CH2:22]([O:24][C:25](=[O:30])[C:26](Br)([CH3:28])[CH3:27])[CH3:23].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[CH2:14]([O:13][C:11]([C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:21][C:26]([C:25]([O:24][CH2:22][CH3:23])=[O:30])([CH3:28])[CH3:27])[CH:8]=2)[NH:3][C:2]=1[CH3:1])=[O:12])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 109239755-Hydroxy-2-methyl-1H-indole-3-carboxylic acid benzyl ester

生成物 1

HCID 233938615-(1-Ethoxycarbonyl-1-methyl-ethoxy)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester収率 49%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

2-Methyl-3-benzyloxycarbonyl-5-hydroxyindole (10.0 g, 35.54 mmol, 1.0 eq) was dissolved in acetonitrile (250 mL), followed by ethyl-2-bromo-isobutyrate (7.63 g, 39.10 mmol, 2.0 eq). Potassium carbonate (9.82 g, 71.08 mmol, 8.7 eq) was also added followed by potassium iodide (catalytic amount). The reaction mixture was refluxed for 24 hours. The reaction mixture was washed with brine and extracted with ethyl acetate (3×100 mL) and dried over sodium sulfate. The product was chromatographed in a hexane to hexane/ethyl acetate 7:3. 6.88 g of the product was obtained, 48% yield.

後処理

  1. temperatureThe reaction mixture was refluxed for 24 hours
  2. washThe reaction mixture was washed with brine
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. dry with materialdried over sodium sulfate
  5. customThe product was chromatographed in a hexane to hexane/ethyl acetate 7:3

出典と根拠

ORDレコード
ord-cb44264314ca42fba20b1323365f41f1
出典データセット
uspto-grants-2005_10
特許番号
US06951848B2

関連ノート

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