[Cl:1][C:2]1[C:7]2[CH:8]=[N:9][NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Br)=[CH:14][CH:13]=1.[H-].[Na+].O>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[C:7]2[CH:8]=[N:9][N:10]([CH2:16][C:15]3[CH:18]=[CH:19][C:12]([F:11])=[CH:13][CH:14]=3)[C:6]=2[CH:5]=[CH:4][N:3]=1
To 4-chloro-1H-pyrazolo[4,3-c]pyridine (60 mg, 0.40 mmol) in 2 ml DMF was added 4-Fluorobenzylbromide (0.060 ml, 0.48 mmol) then add NaH (20 mg, 0.4 mmol) and stir at room temperature overnight. Work up by adding water and EtOAc and extract three times with EtOAc. Pool all organics and wash one time with brine then dry over sodium sulfate, filter and concentrate to dryness. The residue was purified by chromatography over silica gel (eluted with Hexanes/EtOAc 99:1 to 50:50) to provide 38 mg of major isomer A and 15 mg of minor isomer B.
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