Potassium Iodide → 2-Chloro-6-{2-[1-(6-methyl-3-pyridazinyl)-4-piperidinyl]ethoxy}-quinoxaline

HRID 2105912Notes

Reaction equation

HRID 2105912 reaction equation
[Cl:1][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=2)[N:3]=1.Cl[CH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]2[N:23]=[N:24][C:25]([CH3:28])=[CH:26][CH:27]=2)[CH2:18][CH2:17]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH2:14][CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([C:22]4[N:23]=[N:24][C:25]([CH3:28])=[CH:26][CH:27]=4)[CH2:18][CH2:17]3)[CH:8]=2)[N:3]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 149892183-[4-(2-Chloroethyl)-1-piperidinyl]-6-methylpyridazineHCID 135742588HCID 135742588, compound

Product 1

HCID 210777962-Chloro-6-{2-[1-(6-methyl-3-pyridazinyl)-4-piperidinyl]ethoxy}-quinoxalineYield 61.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-chloro-6-hydroxyquinoxaline (52 mg, 288 μmol), 3-[-4-(2-chloroethyl)-1-piperidinyl]-6-methyl pyridazine (76 mg, 317 μmol), potassium iodide (53 mg, 317 μmol) and potassium carbonate (199 mg, 1.44 mmol) in anhydrous dimethylformamide (2 ml) was heated at 90° under an Argon atmosphere for 2 days. Tlc (silica;ethyl acetate) showed new polar material. Removal of the solvent under high vacuum and then chromatography on silica (5 g; eluent: 30% hexane in ethyl acetate) gave the product as a white solid 68 mg (61%).

Workup

  1. temperaturewas heated at 90° under an Argon atmosphere for 2 days
  2. customRemoval of the solvent under high vacuum

Sources & evidence

ORD record
ord-e3fe28e4cde949d3bd33f9cdf1df9771
Source dataset
uspto-grants-2009_08
Patent number
US07579465B2

Reaction notes

Loading…