Potassium Iodide → HCID 58585386, compound

HRID 2252286Notes

Reaction equation

HRID 2252286 reaction equation
Br[CH2:2][CH2:3][OH:4].[Br:5][C:6]1[CH:32]=[CH:31][C:9]([O:10][C:11]2[C:12](=[O:30])[N:13]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[N:14]=[CH:15][C:16]=2[N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[CH:8][CH:7]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.ClCCl>[Br:5][C:6]1[CH:32]=[CH:31][C:9]([O:10][C:11]2[C:12](=[O:30])[N:13]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[N:14]=[CH:15][C:16]=2[N:17]2[CH2:22][CH2:21][N:20]([CH2:2][CH2:3][OH:4])[CH2:19][CH2:18]2)=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 58585181HCID 58585181, compound

Product 1

HCID 58585386HCID 58585386, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

1.35 ml (18.11 mmol) of 2-bromoethanol are added dropwise to a mixture of 4.18 (9.05 mmol) of 4-(4-bromophenoxy)-2-(4-chlorophenyl)-5-(1-piperazinyl)-3(2H)-pyridazinone (Example 57A), 0.15 g of potassium iodide 3.75 g (27.2 mmol) of potassium carbonate in 25 ml of 1,4-dioxane. Stirring under reflux overnight is followed by dilution with dichloromethane and washing twice with water, drying and concentration. Purification is by flash chromatography on silica gel (gradient: dichloromethane/methanol from 99:1 to 97:3).

Workup

  1. temperatureunder reflux overnight
  2. washwashing twice with water
  3. customdrying
  4. concentrationconcentration
  5. customPurification

Sources & evidence

ORD record
ord-4999d071b00f4073844583f54328da0e
Source dataset
uspto-grants-2008_01
Patent number
US07320977B2

Reaction notes

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