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Iodoethane → Methyl 5-bromo-3-(cyclopentyl(ethyl)amino)-2-methylbenzoate

HRID 2208691
Notes
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Reaction equation

HRID 2208691 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([NH:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:18](=O)([O-])[O-].[Cs+].[Cs+].[CH2:24](I)[CH3:25]>CN(C=O)C>[Br:1][C:2]1[CH:11]=[C:10]([N:12]([CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:24][CH3:25])[C:9]([CH3:18])=[C:4]([CH:3]=1)[C:5]([O:7][CH3:8])=[O:6]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 70873691Methyl 3-bromo-5-(cyclopentylamino)benzoate

Product 1

HCID 70872402Methyl 5-bromo-3-(cyclopentyl(ethyl)amino)-2-methylbenzoateYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 3-bromo-5-(cyclopentylamino)benzoate (0.3 g, 0.96 mmol) in DMF (5 mL), cesium carbonate (0.628 g, 1.92 mmol) and ethyl iodide (0.748 g, 4.8 mmol) were added; resulting reaction mass was heated at 80° C. for 24 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 (0.150 g, 46%).

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-85d712532dad4f21b970f58c2b8cd80b
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09376422B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes