Dichloromethane → 2-((3-bromo-4-nitro-1H-indazol-1-yl)methyl)-5-methyl-1,3,4-thiadiazole
Reaction equation
C([N:4]([C:6](=O)[CH2:7][N:8]1[C:16]2[C:11](=[C:12]([N+:17]([O-:19])=[O:18])[CH:13]=[CH:14][CH:15]=2)[C:10]([Br:20])=[N:9]1)[NH2:5])(=O)C.[P+3]=[S:23].C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl.[CH2:33]1[CH2:37]OCC1>>[Br:20][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-:19])=[O:18])[N:8]([CH2:7][C:6]2[S:23][C:37]([CH3:33])=[N:5][N:4]=2)[N:9]=1Participants
Procedure
A suspension of N-acetyl-2-(3-bromo-4-nitro-1H-indazol-1-yl)acetohydrazide (0.4 g) in anhydrous THF (5 mL) was treated at ambient temperature with phosphorus(V) sulfide (0.77 g). The mixture was heated at reflux under a nitrogen atmosphere for 2.5 hours. The reaction mixture was diluted with a large excess of saturated aqueous sodium carbonate solution (50 mL) and DCM (50 mL). The resulting mixture was stirred at ambient temperature for 20 minutes, the phases were separated, and the organic phase was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude material was purified by preparative thin-layer chromatography (silica, 7% MeOH-DCM as eluent) to afford the product (235 mg) as a pale yellow solid.
Workup
- temperatureThe mixture was heated
- temperatureat reflux under a nitrogen atmosphere for 2.5 hours
- customthe phases were separated
- dry with materialthe organic phase was dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe crude material was purified by preparative thin-layer chromatography (silica, 7% MeOH-DCM as eluent)
Sources & evidence
- ORD record
- ord-9af4f55f8b57408da10838e543d28ed6
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08841455B2
Reaction notes
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