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Bromine → N-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethyl)-3-bromoindole-2-carboxamide

HRID 963088
Notes
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Reaction equation

HRID 963088 reaction equation
[Cl:1][C:2]1[CH:35]=[CH:34][CH:33]=[CH:32][C:3]=1[C:4]([C:6]1[CH:10]=[C:9]([CH2:11][CH3:12])[S:8][C:7]=1[N:13]1[C:17]([CH3:18])=[N:16][N:15]=[C:14]1[CH2:19][NH:20][C:21]([C:23]1[NH:24][C:25]2[C:30]([CH:31]=1)=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])=[O:5].[Br:36]Br>C(O)(=O)C>[Cl:1][C:2]1[CH:35]=[CH:34][CH:33]=[CH:32][C:3]=1[C:4]([C:6]1[CH:10]=[C:9]([CH2:11][CH3:12])[S:8][C:7]=1[N:13]1[C:17]([CH3:18])=[N:16][N:15]=[C:14]1[CH2:19][NH:20][C:21]([C:23]1[NH:24][C:25]2[C:30]([C:31]=1[Br:36])=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24408BromineHCID 22439200N-(4-(3-(2-Chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethyl)indole-2-carboxamide

Product 1

HCID 22439220N-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethyl)-3-bromoindole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

N-(4-(3-(2-Chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethyl)indole-2-carboxamide (1.0 g, Example 14) was dissolved in acetic acid (12 ml). Bromine (0.1 ml) dissolved in acetic acid (1 ml) was dropwise added under water-cooling, and the mixture was stirred for 1 hour. The solvent was evaporated, and an aqueous sodium thiosulfate solution was added. The mixture was extracted with chloroform. The extract was washed with saturated brine, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over magnesium sulfate. The solvent was evaporated, and the residue was recrystallized from methanol to give 0.36 g of N-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethyl)-3-bromoindole-2-carboxamide.

Workup

  1. additionwas dropwise added under water-
  2. temperaturecooling
  3. customThe solvent was evaporated
  4. additionan aqueous sodium thiosulfate solution was added
  5. extractionThe mixture was extracted with chloroform
  6. washThe extract was washed with saturated brine
  7. dry with materiala saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-bfbc59867d6142e6a92feb4f4e5937e7
Source dataset
uspto-grants-1998_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05760032

Reaction notes

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