1,1'-Carbonyldiimidazole → 1-(5-Bromonicotinoyl)-3-phenyl-2-pyrazoline
Reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[Br:13][C:14]1[CH:15]=[N:16][CH:17]=[C:18]([CH:22]=1)[C:19]([OH:21])=O.[C:23]1([C:29]2[CH2:33][CH2:32][NH:31][N:30]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C>[Br:13][C:14]1[CH:15]=[N:16][CH:17]=[C:18]([CH:22]=1)[C:19]([N:31]1[CH2:32][CH2:33][C:29]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[N:30]1)=[O:21]Participants
5
Procedure
1,1′-Carbonyldiimidazole (1.7 g) was added to a solution of 5-bromonicotinic acid (2 g) dissolved in DMF (20 ml), at room temperature. The mixture was stirred for 1 hour in a nitrogen atmosphere. To the reaction mixture was dropwise added a solution of 3-phenyl-2-pyrazoline (5.7 g) dissolved in DMF (15 ml), with ice-cooling. The mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated. The residue was dissolved in chloroform. The solution was washed with ice water, dried over anhydrous sodium sulfate, and concentrated. The organic layer was purified by silica gel column chromatography (methanol chloroform=1/100) to obtain 1.4 g of a title compound (yield: 41%).
Workup
- temperaturecooling
- stirringThe mixture was stirred at room temperature for 12 hours
- concentrationThe reaction mixture was concentrated
- dissolutionThe residue was dissolved in chloroform
- washThe solution was washed with ice water
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
- customThe organic layer was purified by silica gel column chromatography (methanol chloroform=1/100)
Sources & evidence
- ORD record
- ord-277104494e4c438a84ec0ef096469f1c
- Source dataset
- uspto-grants-2004_12
- Patent number
- US06831083B2
Reaction notes
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