Potassium Carbonate → 1h-Isoindol-1-one,6-[(3-fluorophenyl)methoxy]-2,3-dihydro-

HRID 1761024Notes

Reaction equation

HRID 1761024 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][NH:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[F:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16][O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][NH:7][C:8]2=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680073-Fluorobenzyl bromideHCID 115283646-Hydroxy-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 117086731h-Isoindol-1-one,6-[(3-fluorophenyl)methoxy]-2,3-dihydro-Yield 83.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6-hydroxy-2,3-dihydro-isoindol-1-one (125.0 mg, 0.84 mmol) and 3-fluorobenzylbromide (174.3 mg, 0.92 mmol) in acetone (5 mL) containing potassium carbonate (276.4 mg, 2.0 mmol) was heated under reflux for 17 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 (180 mg, 83%) as a white solid. MS m/e=258.2 (M+H+).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 17 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-d6837fb75304433bbf474a8ca731aa9d
Source dataset
uspto-grants-2005_01
Patent number
US06846832B2

Reaction notes

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