Sodium Thiosulfate → HCID 22031970, compound

HRID 1792512Notes

Reaction equation

HRID 1792512 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:20]([C:21]3[CH:22]=[CH:23][C:24]4[N:25]([C:27]([C:30]5[S:31][CH:32]=[CH:33][CH:34]=5)=[CH:28][N:29]=4)[CH:26]=3)=[CH:19][N:18]([C:35]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:17]=2)=[CH:12][CH:11]=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C)C=O>[Br:1][C:32]1[S:31][C:30]([C:27]2[N:25]3[CH:26]=[C:21]([C:20]4[C:16]([C:13]5[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=5)=[N:17][N:18]([C:35]([C:42]5[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=5)([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[C:48]5[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=5)[CH:19]=4)[CH:22]=[CH:23][C:24]3=[N:29][CH:28]=2)=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 22031006HCID 22031006, compound

Product 1

HCID 22031970HCID 22031970, compoundYield 108.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

160 mg N-bromosuccinimide was added to 5 mL solution of 500 mg 6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]-3-(2-thienyl)imidazo[1,2-a]pyridine obtained in Example 3 in N,N-dimethylformamide, and the mixture was stirred for 1 hour. An aqueous sodium thiosulfate solution was added thereto and stirred for 30 minutes, and the reaction solution was extracted with ethyl acetate and dried over magnesium sulfate. The residue was purified by NH silica gel column chromatography (hexane/dichloromethane/ethyl acetate) to give 612 mg of the title compound as pale yellow crystals.

Workup

  1. stirringstirred for 30 minutes
  2. extractionthe reaction solution was extracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. customThe residue was purified by NH silica gel column chromatography (hexane/dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-b768aa0dff7c4a4d88657967b41208c1
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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