Potassium Carbonate → N-(3-(trifluoromethyl)benzyl)-2-(2-nitro-5-(pyrrolidin-1-yl)phenyl)-isonicotinamide
Reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[F:12][C:13]([F:41])([F:40])[C:14]1[CH:15]=[C:16]([CH:37]=[CH:38][CH:39]=1)[CH2:17][NH:18][C:19](=[O:36])[C:20]1[CH:25]=[CH:24][N:23]=[C:22]([C:26]2[CH:31]=[C:30](F)[CH:29]=[CH:28][C:27]=2[N+:33]([O-:35])=[O:34])[CH:21]=1>CN(C)C=O.O>[F:40][C:13]([F:12])([F:41])[C:14]1[CH:15]=[C:16]([CH:37]=[CH:38][CH:39]=1)[CH2:17][NH:18][C:19](=[O:36])[C:20]1[CH:25]=[CH:24][N:23]=[C:22]([C:26]2[CH:31]=[C:30]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:29]=[CH:28][C:27]=2[N+:33]([O-:35])=[O:34])[CH:21]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
Into a 10-mL vial, was placed a solution of pyrrolidine (152.5 mg, 2.15 mmol, 3.00 equiv) in N,N-dimethylformamide (5 mL), potassium carbonate (296.2 mg, 2.15 mmol, 3.00 equiv), and N-(3-(trifluoromethyl)benzyl)-2-(5-fluoro-2-nitrophenyl)isonicotinamide 14d (300 mg, 0.72 mmol, 1.00 equiv). The resulting solution was stirred for 4 h at 90° C. in an oil bath. The resulting solution was diluted with 50 mL of water. The resulting solution was extracted with 3×50 mL of ethyl acetate and the organic layers combined. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum to yield 400 mg of crude product as a yellow to green oil.
Workup
- extractionThe resulting solution was extracted with 3×50 mL of ethyl acetate
- dry with materialThe mixture was dried over anhydrous sodium sulfate
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-7ac246350c744fd5b23ea3e4450670ad
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09301951B2
Reaction notes
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