Methyl iodide → HCID 70874128, compound

HRID 2208694Notes

Reaction equation

HRID 2208694 reaction equation
[Cl: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>[Cl: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 70873719HCID 70873719, compound

Product 1

HCID 70874128HCID 70874128, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 5-chloro-3-(cyclopentylamino)-2-methylbenzoate (0.5 g, 1.86 mmol) in acetonitrile (5 mL) was added cesium carbonate (1.22 g, 3.7 mmol) and methyl iodide (1.32 g, 9.33 mmol). The resulting mixture was heated at 80° C. for 12 h. On completion, the mixture was cooled to room temperature and filtered, the residue was washed with ethyl acetate and the filtrate was concentrated and then purified by column chromatography to afford methyl 5-chloro-3-(cyclopentyl(methyl)amino)-2-methylbenzoate (0.5 g, 95%).

Workup

  1. temperatureOn completion, the mixture 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

Sources & evidence

ORD record
ord-c4bc2dbd63c74495a615642b787c42b0
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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