Iodoethane → HCID 86719544, compound

HRID 2208751Notes

Reaction equation

HRID 2208751 reaction equation
[Br:1][C:2]1[C:3]([CH3:19])=[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:20](=O)([O-])[O-].[Cs+].[Cs+].C(I)C>CN(C=O)C>[Br:1][C:2]1[C:3]([CH3:19])=[C:4]([N:13]([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH3:20])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 86719542HCID 86719542, compound

Product 1

HCID 86719544HCID 86719544, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 5-bromo-3-(cyclopentylamino)-2,4-dimethylbenzoate (0.3 g, 1.07 mmol) in DMF (5 mL), cesium carbonate (0.697 g, 2.14 mmol) and ethyl iodide (0.3 mL, 5.38 mmol) were added; resulting reaction mass was heated at 80° C. for 12 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 desired compound (0.3 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-c9c05a420fe546509bab11c9f1972d8d
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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