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Water → tert-butyl 3-(((2-bromo-4-(trifluoromethyl)phenyl)amino)methyl)-2,5-dihydro-1H-pyrrole-1-carboxylate

HRID 1411317
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HRID 1411317 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[Br:12].[H-].[Na+].Cl[CH2:16][C:17]1[CH2:18][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:20][CH:21]=1.O>CN(C)C=O>[Br:12][C:3]1[CH:4]=[C:5]([C:8]([F:9])([F:10])[F:11])[CH:6]=[CH:7][C:2]=1[NH:1][CH2:16][C:17]1[CH2:18][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:20][CH:21]=1
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참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 938992-Bromo-4-trifluoromethylanilineHCID 90449873tert-butyl 3-(chloromethyl)-2,5-dihydro-1H-pyrrole-1-carboxylate

생성물 1

HCID 90449914tert-butyl 3-(((2-bromo-4-(trifluoromethyl)phenyl)amino)methyl)-2,5-dihydro-1H-pyrrole-1-carboxylate수율 37%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매
2회

실험 절차

4-Amino-3-bromobenzotrifluoride (15.0 g, 62.5 mmol) was dissolved in N,N-dimethylformamide (400 mL). Thereafter, sodium hydride (5.0 g, 126 mmol) was added to the above obtained solution under cooling on ice, and the thus obtained mixture was then stirred at room temperature for 2 hours. Thereafter, an N,N-dimethylformamide (30 mL) solution of the tert-butyl 3-(chloromethyl)-2,5-dihydro-1H-pyrrole-1-carboxylate (9.20 g, 42.0 mmol) synthesized by a method described in the known methods (European Journal of Organic Chemistry, 4264-4276; 2008 etc.) or a method similar thereto was further added to the reaction solution under cooling on ice, and the thus obtained mixture was then stirred at room temperature for 3 hours. Subsequently, water was added to the reaction solution, and the mixed solution was then extracted with ethyl acetate. The organic layer was washed with brine, and was then dried over anhydrous sodium sulfate, followed by concentration in vacuo. The obtained residue was purified by silica gel column chromatography (hexane ethyl acetate=3:1) to obtain tert-butyl 3-(((2-bromo-4-(trifluoromethyl)phenyl)amino)methyl)-2,5-dihydro-1H-pyrrole-1-carboxylate (6.46 g, 37%) in the form of a colorless amorphous product.

후처리

  1. temperatureunder cooling on ice
  2. additiona method similar thereto was further added to the reaction solution
  3. temperatureunder cooling on ice
  4. stirringthe thus obtained mixture was then stirred at room temperature for 3 hours
  5. extractionthe mixed solution was then extracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialwas then dried over anhydrous sodium sulfate
  8. concentrationfollowed by concentration in vacuo
  9. customThe obtained residue was purified by silica gel column chromatography (hexane ethyl acetate=3:1)

출처 및 근거

ORD 기록
ord-fac8a3e33f9344848582b7a11b4deddc
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08921576B2

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