Sodium hydride → 1-[6-Fluoro-5-(trifluoromethyl)-2-pyridyl]-6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridine
Reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[N:13]=[CH:12][C:11]3[CH:14]=[N:15][NH:16][C:10]=3[CH:9]=2)[CH:5]=[N:4][CH:3]=1.[H-].[Na+].[F:19][C:20]1[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:23]=[C:22](F)[N:21]=1>CN(C)C=O>[F:19][C:20]1[N:21]=[C:22]([N:16]2[C:10]3[CH:9]=[C:8]([C:6]4[CH:5]=[N:4][CH:3]=[C:2]([CH3:1])[N:7]=4)[N:13]=[CH:12][C:11]=3[CH:14]=[N:15]2)[CH:23]=[CH:24][C:25]=1[C:26]([F:29])([F:27])[F:28]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 6-(6-methylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridine (1.008 mmol; 213.0 mg) in Dimethylformamide (10 mL) at 0° C. was added sodium hydride (60% in mineral oil; 1.210 mmol; 48.40 mg). The resulting mixture was stirred for 10 min. 2,6-difluoro-3-(trifluoromethyl)pyridine (1.008 mmol; 184.6 mg) was then added. The reaction was stirred and allowed to warm to room temperature and stirred for 4 hours. The mixture was quenched with water, and extracted with EtOAc. The organic layer was washed with brine, and then concentrated. The residue was purified on silica eluted with 0 to 100% EtOAc in Heptane. 1-[6-fluoro-5-(trifluoromethyl)-2-pyridyl]-6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridine was obtained as the most abundant isomer (173.6 mg, 46%).
Workup
- stirringThe reaction was stirred
- stirringstirred for 4 hours
- customThe mixture was quenched with water
- extractionextracted with EtOAc
- washThe organic layer was washed with brine
- concentrationconcentrated
- customThe residue was purified on silica
- washeluted with 0 to 100% EtOAc in Heptane
Sources & evidence
- ORD record
- ord-3c93a183b27942998c4961be975e3727
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434725B2
Reaction notes
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