Water → HCID 9843734, compound

HRID 1635993Notes

Reaction equation

HRID 1635993 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[Cl:28])[C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]([O:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH2:17][CH2:18][CH:19]3O)=[CH:12][CH:13]=1)=[O:6].C1C=C[NH+]=CC=1.Br[Br-]Br.O>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[Cl:28])[C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]([O:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH2:17][CH:18]=[CH:19]3)=[CH:12][CH:13]=1)=[O:6]

Participants

4

Reactant 2

HCID 962WaterHCID 9909759HCID 9909759, compound

Product 1

HCID 9843734HCID 9843734, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

1.50 g of 3,4-dichloro-N1-[6-(1-hydroxy-2,3-dihydro-1H-inden-4-yloxy)-3-pyridinyl]benzamide obtained in Example 34 was dissolved in 15 ml of acetic acid, and 1.16 g of pyridinium bromide perbromide was added to the resulting reaction solution and the mixture was stirred at 80° C. After 4 hours, the reaction solution was poured into iced water and extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution, dried over magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane (1:3)) to obtain 430 mg of the titled compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane (1:3))

Sources & evidence

ORD record
ord-721c9cce658f4f7ebc1bb661210a08f6
Source dataset
uspto-grants-2003_01
Patent number
US06511995B1

Reaction notes

Loading…