Water → 4-{4-chloro-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-nitrobenzonitrile
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[C:10]([CH:11]([CH3:13])[CH3:12])[C:3]=12.[H-].[Na+].F[C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([N+:25]([O-:27])=[O:26])[CH:18]=1.O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([N+:25]([O-:27])=[O:26])[CH:18]=3)[N:9]=[C:10]([CH:11]([CH3:13])[CH3:12])[C:3]=12Participants
Procedure
Compound (6b) (0.335 g) was dissolved in DMF (8.6 mL), and sodium hydride (0.097 g, a 55% dispersion in paraffin liquid) was added to the resulting solution at 0° C., followed by stirring for 30 min. Then, 4-fluoro-2-nitrobenzonitrile was added to the reaction solution, followed by stirring at 60° C. for 30 min. Water was added to the reaction solution, and the precipitate was collected by filtration and washed by sprinkling water to obtain 4-{4-chloro-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-nitrobenzonitrile (0.5 g, 85%). 4-{4-Chloro-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-nitrobenzonitrile (0.35 g) and ammonium chloride (0.35 g) were dissolved in a solvent mixture of THF (3 mL), methanol (3 mL), and water (3 mL). Iron (0.57 g) was added to the resulting solution, followed by stirring at 70° C. for 1 hr. Insoluble matters were filtered by celite, and the solvent was distilled away. The precipitate was washed with water and was collected by filtration to obtain compound (106a) (0.32 g, 95%) as a white solid.
Workup
- stirringby stirring at 60° C. for 30 min
- filtrationthe precipitate was collected by filtration
- washwashed
Sources & evidence
- ORD record
- ord-8a1aafcc785948a2b7d61b9ad009af48
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09273045B2
Reaction notes
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