[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=[S:9])[NH2:8].N1C=CC=CC=1.Br[CH:17]([CH:20]=O)[CH:18]=[O:19]>O1CCCC1.CS(C)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[S:9][C:17]([CH:18]=[O:19])=[CH:20][N:8]=1Pyridine-2-carbothioamide (4.5 g) was dissolved in tetrahydrofuran (40 mL). Pyridine (7.9 mL) was added and the reaction was heated to reflux. 2-Bromomalonaldehyde (7.2 g) was added in dimethylsulfoxide (15 mL) dropwise over 10 minutes and the reaction was heated for 3 hours. The reaction was concentrated in vacuo and partitioned between ethyl acetate and sodium hydrogen carbonate aqueous solution. The aqueous layer was back extracted and the combined organic phase was washed with brine and concentrated. The crude reaction was purified by silica gel column chromatography using an eluant of 2% to 4% acetone/dichloromethane to obtain the title compound (2.4 g) with the following physical data.
Loading…
