Methyl iodide → HCID 70872667, compound

HRID 2208761Notes

Reaction equation

HRID 2208761 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:13][CH:14]2[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:19](=O)([O-])[O-].[Cs+].[Cs+].CI>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([N:13]([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH3:19])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 70872494HCID 70872494, compound

Product 1

HCID 70872667HCID 70872667, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 5-bromo-3-(cyclopentylamino)-2-methylbenzoate (1.6 g, 5.38 mmol) in acetonitrile (20 mL), cesium carbonate (3.5 g, 10.73 mmol) and methyl iodide (3.87 g, 27.25 mmol) were added and the resulting reaction mixture heated at 80° C. for 12 h. On completion, the reaction mixture was cooled to room temperature and filtered. The residue was washed with ethyl acetate and filtrate concentrated and purified by column chromatography to afford desired compound (1.6 g, 95%).

Workup

  1. customthe resulting reaction mixture
  2. temperatureOn completion, the reaction mixture was cooled to room temperature
  3. filtrationfiltered
  4. washThe residue was washed with ethyl acetate and filtrate
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-8a31141250454d6488840c724beda6b6
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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