Reaction SMILES: C(O)(=O)C1C=CC=CC=1.[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]([C:19]1[C:20]([CH:25]=[C:26](O)[C:27]2[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=2)=[N:21][CH:22]=[CH:23][CH:24]=1)=[O:18].C(=O)([O-])[O-].[K+].[K+].[N:40]([CH2:43][C:44]1[CH:49]=[C:48]([C:50]([F:53])([F:52])[F:51])[CH:47]=[C:46]([C:54]([F:57])([F:56])[F:55])[CH:45]=1)=[N+:41]=[N-:42].C(O)(C)C>C(O)(C)(C)C>[F:51][C:50]([F:52])([F:53])[C:48]1[CH:49]=[C:44]([CH:45]=[C:46]([C:54]([F:57])([F:55])[F:56])[CH:47]=1)[CH2:43][N:40]1[C:26]([C:27]2[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=2)=[C:25]([C:20]2[C:19]([C:17]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[Cl:10])=[O:18])=[CH:24][CH:23]=[CH:22][N:21]=2)[N:42]=[N:41]1
Reactant: [N-]=[N+]=NCc1cc(C(F)(F)F)cc(C(F)(F)F)c1
Reactant: O=C(c1ccccc1Cl)c1cccnc1C=C(O)c1ccncc1
Agent: O=C(O)c1ccccc1
Agent: O=C([O-])[O-]
Agent: [K+]
Solvent: CC(C)O
Solvent: CC(C)(C)O
Product: O=C(c1ccccc1Cl)c1cccnc1-c1nnn(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)c1-c1ccncc1
Temperature: 70 °C
Reaction time: 1 h
Yield: 79.3 %

Procedure:
Suspend (2-chlorophenyl)-[2-(2-hydroxy-2-pyridin-4-yl-vinyl)pyridin-3-yl]methanone benzoate (204.7 g; 1.04 equiv; 445 mmoles) in t-butanol (614 mL) and treat the slurry with potassium carbonate (124.2 g; 898.6 mmoles). Heat to 70° C. with mechanical stirring for 1 hour. Add 1-azidomethyl-3,5-bistrifluoromethylbenzene (115.6 g; 1.00 equiv; 429.4 mmoles) in a single portion, then heat the mixture to reflux. A circulating bath is used to maintain a condenser temperature of 30° C. After 18 hours at reflux, HPLC reveals that the reaction is complete (<2% 1-azidomethyl-3,5-bistrifluoromethylbenzene remaining). The mixture is cooled to 70° C., isopropanol (818 mL) is added, then the mixture is stirred at 70° C. for 1 hour. The mixture is filtered, and the waste filter cake is rinsed with isopropanol (409 mL). The combined filtrate and washes are transferred to a reactor, and the mechanically stirred contents are heated to 70° C. To the dark purple solution, water (1.84 L) is added slowly over 35 minutes. The solution is cooled to 60° C., then stirred for 1 hour, during which time a thin precipitate forms. The mixture is slowly cooled to RT, then the solid is filtered, washed with 1:1 isopropanol/water (614 mL), subsequently washed with isopropanol (410 mL), then dried in vacuo at 45° C. to produce 200.3 g of crude {2-[1-(3,5-bistrifluoromethylbenzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chlorophenyl)-methanone as a white solid. Crude {2-[1-(3,5-bistrifluoromethylbenzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chlorophenyl)-methanone (200.3 g) and isopropyl acetate (600 mL) are charged to a 5 L 3-neck jacketed flask, then the contents heated to 75° C. After dissolution is achieved, the vessel contents are cooled to 55° C., then the solution polish filtered through a 5 micron filter, and the filter rinsed with a volume of isopropyl acetate (200 mL). After the polish filtration operation is complete, the filtrates are combined, and the vessel contents are adjusted to 50° C. After stirring for at least 15 minutes at 50° C., 0.21 grams of {2-[1-(3,5-bistrifluoromethylbenzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chlorophenyl)-methanone Form IV seed (d90=40 microns) is added, and the mixture stirred at 50° C. for at least 2 h. Heptanes (1.90 L) are then added over at least 2 h. After the heptanes addition is completed, the slurry is stirred for an hour at 50° C., cooled to 23° C. at a rate less then 20° C. per hour, then aged at 23° C. for an hour prior to isolation. The mixture is then filtered in portions through the bottom outlet valve in the reactor into a 600 mL filter. The resulting wetcake is washed portionwise with a solution containing heptanes (420 mL) and isopropyl acetate (180 mL), which is passed directly through the 5 L crystallization vessel. The wetcake is blown dry for 5 minutes with nitrogen, then transferred to a 500 mL plastic bottle. The product is dried at 50° C. for 4 h. to produce 190.3 g of pure {2-[1-(3,5-bistrifluoromethylbenzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chlorophenyl)-methanone, Form IV in 75.0% yield with 100% purity, as determined by HPLC analysis. Particle size is reduced via pin or jet mill. 1H NMR (400 MHz, CDCl3): 5.46 (s, 2H); 7.19 (m, 5H); 7.36 (dd, 1H, J=4.9, 7.8); 7.45 (s, 2H); 7.59 (m, 1H); 7.83 (s, 1H); 7.93 (dd, 1H, J=1.5, 7.8), 8.56 (dd, 1H, J=1.5, 4.9); 8.70 (d, 2H, J=5.9).