Methyl iodide → HCID 70872667, compound

HRID 1959166Notes

Reaction equation

HRID 1959166 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 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of the crude methyl 5-bromo-3-(cyclopentylamino)-2-methylbenzoate (0.7 g, 2.25 mmol) in acetonitrile (15 mL), cesium carbonate (1.47 g, 4.50 mmol) and methyl iodide (1.6 g, 11.26 mmol) were added; resulting reaction mass was heated at 80° C. for 7 h. On completion, reaction mass was cooled to room temperature and filtered, residue was washed with ethyl acetate and filtrate was concentrated and then purified by column chromatography to afford the desired compound (0.6 g, 82%).

Workup

  1. customresulting
  2. customreaction mass
  3. customOn completion, reaction mass
  4. temperaturewas cooled to room temperature
  5. filtrationfiltered
  6. washresidue was washed with ethyl acetate and filtrate
  7. concentrationwas concentrated
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-22a4c7cbb98345f294e92d61f5703a71
Source dataset
uspto-grants-2013_04
Patent number
US08410088B2

Reaction notes

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