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

HRID 1530238ノート

反応式

HRID 1530238 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-24b2072b38b04870b4d5d49fd7b4ba1b
出典データセット
uspto-grants-2015_07
特許番号
US09090562B2

反応ノート

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