Methyl iodide → Methyl 5-bromo-3-(cyclohexyl(methyl)amino)-2-methylbenzoate

HRID 1530216노트

반응식

HRID 1530216 반응식
[Br:1][C:2]1[CH:3]=[C:4]([NH:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C:20](=O)([O-])[O-].[Cs+].[Cs+].CI>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([N:13]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH3:20])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 70872336Methyl 5-bromo-3-(cyclohexylamino)-2-methylbenzoate

생성물 1

HCID 70872437Methyl 5-bromo-3-(cyclohexyl(methyl)amino)-2-methylbenzoate수율 87%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

To a stirred solution of methyl 5-bromo-3-(cyclohexylamino)-2-methylbenzoate (2.75 g, 8.45 mmol) in acetonitrile (25 mL), cesium carbonate (5.45 g, 16.9 mmol) and methyl iodide (6 g, 42.3 mmol) were added; resulting solution was heated at 80° C. for 20 h. On completion, the solution was cooled to room temperature and filtered, and the residue was washed with ethyl acetate. The filtrate was concentrated and then purified by column chromatography to afford methyl 5-bromo-3-(cyclohexyl(methyl)amino)-2-methylbenzoate (2.5 g, 87%).

후처리

  1. temperatureOn completion, the solution was cooled to room temperature
  2. filtrationfiltered
  3. washthe residue was washed with ethyl acetate
  4. concentrationThe filtrate was concentrated
  5. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-de8e67738bbc4c67b06d4eac27d3489f
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090562B2

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