Water → 5-(4-Aminophenylthio)-2-methylimidazo[1,2-a]pyridine

HRID 856664Notes

Reaction equation

HRID 856664 reaction equation
Cl[C:2]1[N:7]2[CH:8]=[C:9]([CH3:11])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([SH:19])=[CH:15][CH:14]=1.C(N(CC)CC)C.O>CN(C=O)C>[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][C:2]2[N:7]3[CH:8]=[C:9]([CH3:11])[N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 145104-AminothiophenolHCID 139119055-Chloro-2-methylimidazo[1,2-A]pyridine

Product 1

HCID 229388015-(4-Aminophenylthio)-2-methylimidazo[1,2-a]pyridineYield 67.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-chloro-2-methylimidazo[1,2-a]pyridine (1.0 g) and 4-aminothiophenol (3.25 g) and triethylamine (1.7 ml) in DMF (10 ml) was stirred for 3 days at 90° C. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was separated and purified by column chromatography (ethyl acetate:hexane 2:1→ethyl acetate→ethanol:ethyl acetate 1:9), to give 5-(4-aminophenylthio)-2-methylimidazo[1,2-a]pyridine (1.04 g) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was separated
  6. custompurified by column chromatography (ethyl acetate:hexane 2:1→ethyl acetate→ethanol:ethyl acetate 1:9)

Sources & evidence

ORD record
ord-089064e8cbc84db499fee957253a0c33
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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