Potassium Carbonate → Methyl 4-chloro-3'-((2-cyclopentyl-1-oxoisoindolin-5-yloxy)methyl)biphenyl-3-carboxylate

HRID 404956Notes

Reaction equation

HRID 404956 reaction equation
[CH:1]1([N:6]2[CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([OH:15])[CH:12]=3)[C:7]2=[O:16])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:24][C:25]1[CH:26]=[C:27]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([C:38]([O:40][CH3:41])=[O:39])[CH:32]=2)[CH:28]=[CH:29][CH:30]=1>CC(C)=O>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([CH2:24][O:15][C:11]3[CH:12]=[C:13]4[C:8](=[CH:9][CH:10]=3)[C:7](=[O:16])[N:6]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH2:14]4)[CH:26]=2)=[CH:32][C:33]=1[C:38]([O:40][CH3:41])=[O:39]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 509936542-Cyclopentyl-5-hydroxyisoindolin-1-oneHCID 50994825Methyl 3'-(bromomethyl)-4-chlorobiphenyl-3-carboxylate

Product 1

HCID 50993811Methyl 4-chloro-3'-((2-cyclopentyl-1-oxoisoindolin-5-yloxy)methyl)biphenyl-3-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-cyclopentyl-5-hydroxyisoindolin-1-one (50 mg, 0.23 mmol) in acetone (15 mL), K2CO3 (181 mg, 1.31 mmol) was added methyl 3′-(bromo-methyl)-4-chlorobiphenyl-3-carboxylate (92 mg, 0.27 mmol) and the mixture was heated at reflux for 1 h. The reaction mixture was filtered and the solvent was evaporated in vacuo to obtain methyl 4-chloro-3′-((2-cyclopentyl-1-oxoisoindolin-5-yloxy)methyl)biphenyl-3-carboxylate as a yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 h
  3. filtrationThe reaction mixture was filtered
  4. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-15191c0d6e134eacb166e0a12fb8e4ca
Source dataset
uspto-grants-2014_06
Patent number
US08748632B2

Reaction notes

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