Methyl iodide → HCID 86719540, compound

HRID 2208722Notes

Reaction equation

HRID 2208722 reaction equation
[CH:1]1([NH:6][C:7]2[C:8]([CH3:21])=[C:9]([CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=2)[C:10]([O:12][CH3:13])=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:22](=O)([O-])[O-].[Cs+].[Cs+].CI>C(#N)C>[CH:1]1([N:6]([CH3:22])[C:7]2[C:8]([CH3:21])=[C:9]([CH:14]=[C:15]([C:17]([F:18])([F:19])[F:20])[CH:16]=2)[C:10]([O:12][CH3:13])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 70873966HCID 70873966, compound

Product 1

HCID 86719540HCID 86719540, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 3-(cyclopentylamino)-2-methyl-5-(trifluoromethyl)benzoate (1.6 g, 5.38 mmol) in acetonitrile (25 mL) was added cesium carbonate (3.5 g, 10.7 mmol) and methyl iodide (3.8 g, 26.8 mmol). The mixture was heated at 80° C. for 8 h. On completion, the reaction was cooled to room temperature and filtered. The residue was washed with ethyl acetate and the filtrate was concentrated to give methyl 3-(cyclopentyl(methyl)amino)-2-methyl-5-(trifluoromethyl)benzoate.

Workup

  1. temperatureOn completion, the reaction was cooled to room temperature
  2. filtrationfiltered
  3. washThe residue was washed with ethyl acetate
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a82332355ca444e6aa76bfe7c70c2e07
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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