Potassium Carbonate → HCID 66799705, compound

HRID 404958Notes

Reaction equation

HRID 404958 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]([B:31]([OH:33])[OH:32])[CH:28]=[CH:29][CH:30]=1>CC(C)=O>[CH:1]1([N:6]2[CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([O:15][CH2:24][C:25]4[CH:26]=[C:27]([B:31]([OH:33])[OH:32])[CH:28]=[CH:29][CH:30]=4)[CH:12]=3)[C:7]2=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27732813-(Bromomethyl)benzeneboronic acidHCID 50993654HCID 50993654, compound

Product 1

HCID 66799705HCID 66799705, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-cyclopentyl-5-hydroxyisoindolin-1-one (500 mg, 2.3 mmol) in acetone (20 mL), K2CO3 (1.2 g, 8.7 mmol) and 3-(bromomethyl)phenylboronic acid (650 mg, 3.0 mmol) were added and refluxed for 3 h. The reaction mixture was filtered and solvent was evaporated in vacuo to obtain 3-((2-cyclopentyl-1-oxoisoindolin-5-yloxy)methyl)phenylboronic acid as a white solid (582.7 mg, 72%). The crude product was used for the next step without further purification. 1H NMR (400 MHz, DMSO-d6): δ 7.86 (s, 1H), 7.75-7.69 (m, 2H), 7.55-7.32 (m, 4H), 7.19 (s, 1H), 7.09-7.07 (m, 1H), 5.15 (s, 2H), 4.55-4.49 (m, 1H), 4.37 (s, 2H), 1.84-1.56 (m, 8H). LRMS calcd. for C20H22BNO4 [M+H]+ 352 found: 352.

Workup

  1. temperaturerefluxed for 3 h
  2. filtrationThe reaction mixture was filtered
  3. customsolvent was evaporated in vacuo

Sources & evidence

ORD record
ord-b65aeafc2acf4842ae27c8e187a05106
Source dataset
uspto-grants-2014_06
Patent number
US08748632B2

Reaction notes

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