Dimethylformamide → 4-(7-Chlorothieno[3,2-b]pyridin-2-yl)-1-ethyl-1H-imidazole-2-carbaldehyde
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:12]=[CH:13][N:14]([CH2:16][CH3:17])[CH:15]=3)[S:10][C:3]=12.C([Li])CCC.CN(C)[CH:25]=[O:26]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:12]=[C:13]([CH:25]=[O:26])[N:14]([CH2:16][CH3:17])[CH:15]=3)[S:10][C:3]=12Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 7-chloro-2-(1-ethyl-1H-imidazol-4-yl)thieno[3,2-b]pyridine (13, scheme 4) (1.50 g, 5.69 mmol) in tetrahydrofuran at −78° C. (1.3 mL) was added n-Butyllithium (3.4 mL, 8.53 mmol) and the reaction mixture was stirred for about 15 minutes. Dimethylformamide (0.66 mL, 8.53 mmol) was added slowly and the reaction mixture was stirred at −78° C. until completion of the reaction. The mixture was warmed to room temperature and quenched with water. The precipitate was removed by filteration, washed with water and dried well. The crude product was purified by trituration with dichloromethane, filtered, washed with additional dichloromethane and dried to afford the title compound 111 as a yellow solid (682 mg, 41% yield). MS (m/z): 291.9 (M+H).
Workup
- stirringthe reaction mixture was stirred at −78° C. until completion of the reaction
- customquenched with water
- customThe precipitate was removed by filteration
- washwashed with water
- customdried well
- customThe crude product was purified by trituration with dichloromethane
- filtrationfiltered
- washwashed with additional dichloromethane
- customdried
Sources & evidence
- ORD record
- ord-4ee9dae830914ff0bb09255bd9700280
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093264B2
Reaction notes
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