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

HRID 966499

반응식

HRID 966499 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cb44264314ca42fba20b1323365f41f1
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06951848B2

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