[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][OH:11])[CH:5]=[N:6][C:7]=1[O:8][CH3:9].[H-].[Na+].[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1F)[C:18]#[N:19]>CN(C=O)C>[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[O:11][CH2:10][C:4]1[CH:5]=[N:6][C:7]([O:8][CH3:9])=[C:2]([Cl:1])[CH:3]=1)[C:18]#[N:19]To a solution of 5-chloro-3-hydroxymethyl-6-methoxypyridine (50 mg, 0.29 mmol) in DMF (3 mL) was added sodium hydride dispersion in oil (60%, 13.8 mg, 0.576 mmol) and the reaction stirred at 0° C. for 30 minutes. 3-Chloro-4-fluorobenzonitrile (45 mg, 0.288 mmol) was then added and the reaction stirred, warming to room temperature for 2 hours. The reaction was poured onto water (10 mL) and extracted with EtOAc (10 mL), dried over sodium sulfate and concentrated in vacuo to afford the title compound (89 mg, 72%).
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