[CH2:1]([N:8]1[C:12]([NH2:13])=[CH:11][N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:14][C:15]1[CH:16]=[CH:17][C:18](F)=[C:19]([CH:22]=1)[C:20]#[N:21].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[CH2:1]([N:8]1[C:12]([NH:13][C:18]2[CH:17]=[CH:16][C:15]([Cl:14])=[CH:22][C:19]=2[C:20]#[N:21])=[CH:11][N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=11-Benzyl-1H-1,2,3-triazol-5-amine 5a (1.00 g, 5.74 mmol) and 5-chloro-2-fluoro-benzonitrile (892.9 mg, 5.74 mmol) were combined in THF (6 mL) and cooled to −78° C. LiHMDS (6.31 mL of 1 M, 6.31 mmol) was added dropwise and the reaction stirred for 5 min and then allowed to warm to room temperature and subsequently heated at 60° C. for 1 h. The mixture was quenched water and then evaporated and the residue partitioned between EtOAc and 1M HCl, the organic layer separated and concentrated. Trituration of the residue in EtOAc and hexanes afforded 2-[(3-benzyltriazol-4-yl)amino]-5-chloro-benzonitrile as a brown solid (1.06 g, 60%). MS m/z: 310.1 (M+H)+.
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