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Water → HCID 18923432, compound

HRID 1899999
Notes
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Reaction equation

HRID 1899999 reaction equation
[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]([NH:20][C:21](=[O:23])[CH3:22])[C:14]=3[Cl:24])[C:5]2=[N:4][C:3]=1[CH3:25].[H-].[Na+].Br[CH2:29][C:30]([O:32]CC)=[O:31].O>CN(C)C=O.C(O)C.[OH-].[Na+]>[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]([N:20]([CH2:29][C:30]([OH:32])=[O:31])[C:21](=[O:23])[CH3:22])[C:14]=3[Cl:24])[C:5]2=[N:4][C:3]=1[CH3:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 10836951HCID 10836951, compound

Product 1

HCID 18923432HCID 18923432, compoundYield 59.7%

Reagents, catalysts & solvents 3

HCID 702Ethanol
Solvent
HCID 6228DimethylformamideSolvent
HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 3-bromo-8-(2,6-dichloro-3-acetylaminobenzyloxy)-2-methylimidazo[1,2-a]pyridine (222 mg) in N,N-dimethylformamide (2 ml) was added sodium hydride (24 mg, 60% oil dispersion) at ambient temperature. The mixture was stirred for half an hour at the same temperature and then ethyl bromoacetate (100 mg) was added thereto in one portion. The mixture was stirred for 2 hours at the same temperature and poured into water. The separated oil was extracted with dichloromethane. The extract was washed with water, dried, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to give an oil, which was dissolved in a mixture of ethanol (10 ml) and 1N sodium hydroxide solution (2 ml). The solution was refluxed for one and half hour. The organic solvent was removed under reduced pressure. The aqueous layer was adjusted to pH 4 with diluted hydrochloric acid to give 3-bromo-8-[2,6-dichloro-3-(N-carboxymethyl-N-acetylamino)benzyloxy]-2-methylimidazo[1,2-a]pyridine (150 mg) as a white solid.

Workup

  1. stirringThe mixture was stirred for 2 hours at the same temperature
  2. extractionThe separated oil was extracted with dichloromethane
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel
  7. customto give an oil, which
  8. temperatureThe solution was refluxed for one and half hour
  9. customThe organic solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c6a8dd05e8584e8bbd6e7c22c9bb0e63
Source dataset
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05574042

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes