Methyl iodide → HCID 70913288, compound

HRID 2208785Notes

Reaction equation

HRID 2208785 reaction equation
[Br:1][C:2]1[C:11]([NH:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:18](=O)([O-])[O-].[Cs+].[Cs+].CI>C(#N)C>[Br:1][C:2]1[C:11]([N:12]([CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH3:18])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 70873949HCID 70873949, compound

Product 1

HCID 70913288HCID 70913288, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 2-bromo-3-(cyclopentylamino)benzoate (1.4 g, 4.69 mmol) in acetonitrile (20 mL), cesium carbonate (3.0 g, 9.2 mmol) and methyl iodide (3.38 g, 23.4 mmol) were added and the resulting reaction mixture heated at 80° C. for 12 h. On completion, the mixture was cooled to room temperature and filtered and the residue washed with ethyl acetate. The filtrate was concentrated and then purified by column chromatography to afford desired methyl 2-bromo-3-(cyclopentyl(methyl)amino)benzoate (1.1 g, 75%).

Workup

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

Sources & evidence

ORD record
ord-72df6afcf0ec4c1587fe62b338b96bbd
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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