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

HRID 5484Notes

Reaction equation

HRID 5484 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-af87d36622ea458291f1775ee5fc3fe3
Source dataset
uspto-grants-1993_09
Patent number
US05244908

Reaction notes

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