Potassium Carbonate → HCID 22397101, compound

HRID 1070691Notes

Reaction equation

HRID 1070691 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=O)[NH:6][C:5]2=[O:12].[C:13](=[O:16])([O-])[O-].[K+].[K+].[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1>C(O)C>[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:7][N:6]2[C:5](=[O:12])[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([O:1][CH2:24][C:23]4[CH:26]=[CH:27][C:20]([F:19])=[CH:21][CH:22]=4)[CH:3]=3)[C:13]2=[O:16])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 105589505-Hydroxyisoindoline-1,3-dione

Product 1

HCID 22397101HCID 22397101, compoundYield 6.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-hydroxy-isoindole-1,3-dione (200 mg, 1.0 mmol), potassium carbonate (178 mg, 1.05 mmol), 4-fluorobenzylbromide (204 mg, 1.05 mmol) in ethanol (5 mL) was heated at 80° C. overnight. After cooling to room temperature, the reaction mixture was filtered and evaporated. The residue was purified by chromatography (SiO2, heptane-CH2Cl2 2:3 then CH2Cl2— 2N NH3-MeOH 99:1: to 95:5) to afford the title compound (13 mg, 3%) as a white solid. MS: m/e=379.4 (M+).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered
  3. customevaporated
  4. customThe residue was purified by chromatography (SiO2, heptane-CH2Cl2 2:3

Sources & evidence

ORD record
ord-a09de569a9ae4bf18bf06ed61962c154
Source dataset
uspto-grants-2005_06
Patent number
US06903095B2

Reaction notes

Loading…