N-bromobutanimide → 3-Bromo-5-[2-(isopropyloxycarbonylamino)ethylthio]imidazo[1,2-a]pyridine

HRID 1081756Notes

Reaction equation

HRID 1081756 reaction equation
[CH:1]([O:4][C:5]([NH:7][CH2:8][CH2:9][S:10][C:11]1[N:16]2[CH:17]=[CH:18][N:19]=[C:15]2[CH:14]=[CH:13][CH:12]=1)=[O:6])([CH3:3])[CH3:2].[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:20][C:17]1[N:16]2[C:11]([S:10][CH2:9][CH2:8][NH:7][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[O:6])=[CH:12][CH:13]=[CH:14][C:15]2=[N:19][CH:18]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 233628125-[2-(Isopropyloxycarbonylamino)ethylthio]imidazo[1,2-a]pyridine

Product 1

HCID 233628553-Bromo-5-[2-(isopropyloxycarbonylamino)ethylthio]imidazo[1,2-a]pyridineYield 82.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5-[2-(isopropyloxycarbonylamino)ethylthio]imidazo[1,2-a]pyridine (279 mg, 1 mmole) in chloroform (5 ml) was added N-bromosuccinimide (187 ml, 1.05 mmoles) and the mixture was stirred at room temperature for 1 hour. The reaction solution was washed with water and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography (eluent:ethyl acetate) to obtain 296 mg of the desired product (82.7%, colorless solid).

Workup

  1. washThe reaction solution was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationAfter the solvent was distilled off
  4. customthe residue was purified by column chromatography (eluent:ethyl acetate)

Sources & evidence

ORD record
ord-9d36f906bf114ba6a167611aa9178079
Source dataset
uspto-grants-1996_12
Patent number
US05587383

Reaction notes

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