Potassium Carbonate → HCID 22594218, compound

HRID 1761008Notes

Reaction equation

HRID 1761008 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[NH:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].[F:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22]Br>CC(C)=O>[F:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[NH:6][CH2:5]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680073-Fluorobenzyl bromideHCID 225942075-Hydroxy-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 22594218HCID 22594218, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5-hydroxy-2,3-dihydro-isoindol-1-one (2.4 g, 16 mmol), potassium carbonate (2.4 g, 18 mmol) and 3-fluorobenzyl bromide (3.3 g, 18 mmol) in acetone (40 mL) was heated under reflux for 22 h. After cooling to RT the mixture was filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2:2N NH3-MeOH 90:10) to afford the title product (2.8 g, 67%) as a white solid. MS m/e=257.2 (M+).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 22 h
  3. filtrationwas filtered
  4. customevaporated
  5. customThe residue was purified by chromatography (SiO2, CH2Cl2:2N NH3-MeOH 90:10)

Sources & evidence

ORD record
ord-0f959918c71849528d6c7137ad7037ba
Source dataset
uspto-grants-2005_01
Patent number
US06846832B2

Reaction notes

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