Methyl iodide → HCID 70873789, compound

HRID 2208790Notes

Reaction equation

HRID 2208790 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]([Cl: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]([Cl:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 70873993HCID 70873993, compound

Product 1

HCID 70873789HCID 70873789, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 5-bromo-2-chloro-3-(cyclopentylamino)benzoate (0.550 g, 1.65 mmol) in acetonitrile (20 mL) was added cesium carbonate (1.08 g, 3.31 mmol) and methyl iodide (1.17 g, 8.25 mmol). The reaction mixture was 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 the filtrate was concentrated and purified by column chromatography to afford methyl 5-bromo-2-chloro-3-(cyclopentyl(methyl)amino)benzoate (0.350 g, 61%).

Workup

  1. temperatureOn completion, the reaction 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-8a449209f42e4dd79db41c31330b5174
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

Loading…