1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → 2-(2-(6-(2-Fluorophenyl)pyridin-3-yloxy)ethyl)isoindole-1,3-dione

HRID 1896708Notes

Reaction equation

HRID 1896708 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.BrC1C=CC([N+]([O-])=O)=CN=1.FC1C=CC=CC=1B(O)O.C(=O)([O-])[O-].[K+].[K+].Br[CH2:42][CH2:43][N:44]1[C:52](=[O:53])[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[C:45]1=[O:54]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[CH:12][C:11]([O:14][CH2:42][CH2:43][N:44]2[C:45](=[O:54])[C:46]3[C:51](=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:52]2=[O:53])=[CH:10][CH:9]=1

Participants

7

Reactant 5

HCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium CarbonateHCID 782402-Bromo-5-nitropyridineHCID 27343542-Fluorophenylboronic acidHCID 231457706-(2-Fluorophenyl)pyridin-3-ol

Product 1

HCID 597613522-(2-(6-(2-Fluorophenyl)pyridin-3-yloxy)ethyl)isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

500 mg (2.64 mmol) of 6-(2-fluorophenyl)pyridin-3-ol (prepared from 2-bromo-5-nitropyridine and 2-fluorophenylboronic acid; the nitro group was converted into the hydroxy group according to the method described in WO 98/25920), 730.6 mg (5.28 mmol) of potassium carbonate and 738.6 mg (2.91 mmol) of 2-(2-bromoethyl)-isoindole-1,3-dione in 10 ml of DMF were stirred at room temperature for 4 h. The solvent was removed by evaporation and the residue treated with ethyl acetate and water. The organic layer was evaporated and the residue purified by chromatography. Yield: 189 mg.

Workup

  1. customThe solvent was removed by evaporation
  2. additionthe residue treated with ethyl acetate and water
  3. customThe organic layer was evaporated
  4. customthe residue purified by chromatography

Sources & evidence

ORD record
ord-d2ac8837ecf24754aafcb474072790a7
Source dataset
uspto-grants-2013_08
Patent number
US08518976B2

Reaction notes

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