Dimethylformamide → 2-(4-bromobenzyl)-1-propyl-1H-imidazole-4-carboxylic acid ethyl ester

HRID 250812노트

반응식

HRID 250812 반응식
C(=O)([O-])[O-].[K+].[K+].I[CH2:8][CH2:9][CH3:10].[CH2:11]([O:13][C:14]([C:16]1[N:17]=[C:18]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=2)[NH:19][CH:20]=1)=[O:15])[CH3:12].CN(C=O)C>CCOC(C)=O>[CH2:11]([O:13][C:14]([C:16]1[N:17]=[C:18]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([Br:28])=[CH:26][CH:27]=2)[N:19]([CH2:8][CH2:9][CH3:10])[CH:20]=1)=[O:15])[CH3:12].[CH2:11]([O:13][C:14]([C:16]1[N:17]([CH2:8][CH2:9][CH3:10])[C:18]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([Br:28])=[CH:26][CH:27]=2)=[N:19][CH:20]=1)=[O:15])[CH3:12]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 178469892HCID 178469892, 화합물

생성물 2

HCID 580889072-(4-bromobenzyl)-1-propyl-1H-imidazole-4-carboxylic acid ethyl ester수율 33.6%HCID 672311902-(4-bromobenzyl)-3-propyl-3H-imidazole-4-carboxylic acid ethyl ester수율 20%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

Potassium carbonate (2.6 g, 18.7 mmol) and 1-iodopropane (669.7 μL, 6.9 mmol) were added to 2-(4-Bromobenzyl)-1H-imidazole-4-carboxylic acid ethyl ester (1.9 g, 6.2 mmol) dissolved in DMF (40 mL, 500 mmol). The mixture was heated at 60° C. for 5 hours. The mixture was cooled and then diluted with EtOAc (100 mL), washed with water and saturated aqueous NaCl (100 mL each), dried over MgSO4, filtered and concentrated. The mixture was purified by column chromatography (20-60% EtOAc in Hexanes) to yield the desired product, 2-(4-bromobenzyl)-1-propyl-1H-imidazole-4-carboxylic acid ethyl ester (736 mg, 33.6% yield), and its regioisomer, 2-(4-bromobenzyl)-3-propyl-3H-imidazole-4-carboxylic acid ethyl ester (500 mg, 20% yield). The structures were confirmed by NMR.

후처리

  1. temperatureThe mixture was cooled
  2. washwashed with water and saturated aqueous NaCl (100 mL each)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe mixture was purified by column chromatography (20-60% EtOAc in Hexanes)

출처 및 근거

ORD 기록
ord-8e636dd383b443f1b8819ab032213906
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863309B2

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