HCID 90461968, compound → HCID 117607155, compound

HRID 588792Notes

Reaction equation

HRID 588792 reaction equation
[Cl:1][C:2]1[C:28]([Cl:29])=[CH:27][C:5]([O:6][C:7]2[CH:12]=[C:11]([O:13][CH2:14][CH2:15][N:16]3C(=O)C4C(=CC=CC=4)C3=O)[CH:10]=[CH:9][N:8]=2)=[C:4]([I:30])[CH:3]=1>CCO>[Cl:1][C:2]1[C:28]([Cl:29])=[CH:27][C:5]([O:6][C:7]2[CH:12]=[C:11]([O:13][CH2:14][CH2:15][NH2:16])[CH:10]=[CH:9][N:8]=2)=[C:4]([I:30])[CH:3]=1

Participants

3

Reactant 1

HCID 90461968HCID 90461968, compound

Product 1

HCID 117607155HCID 117607155, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 2-(2-(2-(4,5-dichloro-2-iodophenoxy)pyridin-4-yloxy)ethyl)isoindoline-1,3-dione (120 mg, 0.22 mmol), N2H4.H2O (106 mg, 1.80 mmol) and EtOH (5 mL) was stirred at reflux for 1 h. The mixture was allowed to cool to room temperature and then concentrated in vacuo. The residue was slurried in DCM (5 mL) and MeOH (1 mL). The precipitate was removed by filtration, and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (DCM/MeOH=10:1) to afford the desired product (35 mg, 38% yield).

Workup

  1. temperatureat reflux for 1 h
  2. concentrationconcentrated in vacuo
  3. customThe precipitate was removed by filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel (DCM/MeOH=10:1)

Sources & evidence

ORD record
ord-926d235f12224ea9932dc121dca52f8c
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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