Iodoethane → Methyl 5-bromo-3-(cyclopentyl(ethyl)amino)-2-methylbenzoate

HRID 1530238노트

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HRID 1530238 반응식
[Br:1][C:2]1[CH:3]=[C:4]([NH:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([O-:9])=[O:8].[C:18](=O)([O-])[O-].[Cs+].[Cs+].[CH2:24](I)[CH3:25]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([N:12]([CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:24][CH3:25])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:18])=[O:8]

참가 물질

5

반응물 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 866726525-Bromo-3-(cyclopentylamino)-2-methylbenzoate

생성물 1

HCID 70872402Methyl 5-bromo-3-(cyclopentyl(ethyl)amino)-2-methylbenzoate수율 32.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a stirred solution of 5-bromo-3-(cyclopentylamino)-2-methylbenzoate (2 g, 6.43 mmol) in DMF (15 mL), cesium carbonate (4.18 g, 12.8 mmol) and ethyl iodide (5.01 g, 32.15 mmol) were added; the resulting reaction mixture was heated at 80° C. for 18 h. On completion, the reaction mixture was cooled to room temperature and filtered, residue was washed with ethyl acetate and filtrate was concentrated to afford desired crude compound, which was purified by column chromatography at afford methyl 5-bromo-3-(cyclopentyl(ethyl)amino)-2-methylbenzoate (0.7 g, 32.1%).

후처리

  1. customthe resulting reaction mixture
  2. temperatureOn completion, the reaction mixture was cooled to room temperature
  3. filtrationfiltered
  4. washresidue was washed with ethyl acetate and filtrate
  5. concentrationwas concentrated
  6. customto afford desired crude compound, which
  7. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-24b2072b38b04870b4d5d49fd7b4ba1b
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090562B2

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