1,1'-Carbonyldiimidazole → HCID 53303681, compound

HRID 1025545Notes

Reaction equation

HRID 1025545 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([C:12]([OH:14])=O)[C:9]([OH:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.N1(C(N2C=CN=C2)=O)C=CN=C1.[CH2:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30][NH:29]1>C1COCC1>[Br:1][C:2]1[CH:11]=[C:10]([C:12]([N:29]2[CH2:30][C:31]3[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:28]2)=[O:14])[C:9]([OH:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 422478IsoindolineHCID 145347685-Bromo-8-hydroxyquinoline-7-carboxylic acid

Product 1

HCID 53303681HCID 53303681, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-bromo-8-hydroxyquinoline-7-carboxylic acid of Preparation 4 (150 mg, 0.56 mmol) and di(1H-imidazol-1-yl)methanone (90.7 mg, 0.56 mmol) in THF (10 mL) was heated to reflux for 3 h, under nitrogen. The reaction mixture was allowed to cool to RT and isoindoline (53 mg, 0.45 mmol) was added. The resulting mixture was stirred at RT overnight. The reaction mixture was then quenched with H2O and an aqueous saturated solution of sodium hydrogen carbonate, and twice extracted with DCM. The separated organics were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by SPE-SI cartridge (2 g, DCM to DCM:MeOH 99:1) affording the title compound (39.1 mg, 0.11 mmol) as a light brown solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h, under nitrogen
  3. customThe reaction mixture was then quenched with H2O
  4. extractionan aqueous saturated solution of sodium hydrogen carbonate, and twice extracted with DCM
  5. dry with materialThe separated organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by SPE-SI cartridge (2 g, DCM to DCM:MeOH 99:1)

Sources & evidence

ORD record
ord-e08162a25a1a42ccb5eb8c4a19ed00ee
Source dataset
uspto-grants-2014_05
Patent number
US08729098B2

Reaction notes

Loading…