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

HRID 1616370ノート

反応式

HRID 1616370 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-35b2b04f74334598aa0f80472906e14e
出典データセット
uspto-grants-2014_07
特許番号
US08765732B2

反応ノート

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