Reaction SMILES: [CH2:1]([N:3]1[CH2:8][CH2:7][CH:6]([CH2:9][C:10]2[N:15]3[N:16]=[C:17]([NH:19][C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=4)[N:18]=[C:14]3[CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:4]1)[CH3:2].C(N1CCC(=C)CC1)C1C=CC=CC=1.Br[C:45]1[N:50]2[N:51]=[C:52]([NH:54][C:55]3[CH:60]=[CH:59][C:58]([C:61]([F:64])([F:63])[F:62])=[CH:57][CH:56]=3)[N:53]=[C:49]2[CH:48]=[CH:47][CH:46]=1.C1(NC2N=C3C=CC=C(CC4CCNCC4)N3N=2)C=CC=CC=1.C(N1CCC(CC2N3N=C(NC4C=CC(C(F)(F)F)=CC=4)N=C3C=CC=2)CC1)C1C=CC=CC=1.N1CCC(CC2N3N=C(NC4C=CC(C(F)(F)F)=CC=4)N=C3C=CC=2)CC1>C(O)C.[Pd].C(O)(=O)C>[CH2:1]([N:3]1[CH2:4][CH2:5][CH:6]([CH2:9][C:10]2[N:15]3[N:16]=[C:17]([NH:19][C:20]4[CH:21]=[CH:22][C:23]([C:26]([F:28])([F:27])[F:29])=[CH:24][CH:25]=4)[N:18]=[C:14]3[CH:13]=[CH:12][CH:11]=2)[CH2:7][CH2:8]1)[CH3:2].[F:64][C:61]([F:62])([F:63])[C:58]1[CH:59]=[CH:60][C:55]([NH:54][C:52]2[N:53]=[C:49]3[CH:48]=[CH:47][CH:46]=[CH:45][N:50]3[N:51]=2)=[CH:56][CH:57]=1
Reactant: FC(F)(F)c1ccc(Nc2nc3cccc(Br)n3n2)cc1
Agent: [Pd]
Agent: C=C1CCN(Cc2ccccc2)CC1
Agent: CCN1CCC(Cc2cccc3nc(Nc4ccc(C(F)(F)F)cc4)nn23)CC1
Solvent: CCO
Solvent: CC(=O)O
Product: FC(F)(F)c1ccc(Nc2nc3ccccn3n2)cc1
Temperature: 25 °C
Reaction time: 8 h
Yield: 13.29 %

Procedure:
5-((1-Ethylpiperidin-4-yl)methyl)-N-(4-(trifluoromethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine. 541-Benzylpiperidin-4-yl)methyl)-N-(4-(trifluoromethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine was synthesized from 1-benzyl-4-methylenepiperidine and 5-bromo-N-(4-(trifluoromethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine following the procedure described for N-phenyl-5-(piperidin-4-ylmethyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine. 5-((1-Benzylpiperidin-4-yl)methyl)-N-(4-(trifluoromethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine (0.165 g, 0.354 mmol) was dissolved in ethanol (30 mL) and treated with a catalytic amount of palladium on carbon (10 weight %). The reaction was stirred under an atmosphere of hydrogen gas overnight at room temperature. As only trace conversion was observed, a drop of acetic acid was added and the reaction was stirred at room temperature overnight. Most of the starting material was converted to the title compound contaminated with a minor amount of 5-(piperidin-4-ylmethyl)-N-(4-(trifluoromethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine. The catalyst was removed by filtration washed with methanol and the filtrate was concentrated under reduced pressure. The residue was purified by semi-preparative HPLC (20-70% acetonitrile+0.1% trifluoroacetic acid in water+0.1% trifluoroacetic acid, 3 injections, 30 min.). The desired fractions were combined and neutralized with a STRATA cationic resin exchange column. The eluate was concentrated under reduced pressure and dried in a vacuum oven for 5 h. 541-Ethylpiperidin-4-yl)methyl)-N-(4-(trifluoromethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine (0.019 g, 0.047 mmol, 13.29% yield) was isolated as a off-white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm) 10.18 (s, 1H), 7.91 (d, J=8.59 Hz, 2H), 7.64 (d, J=8.59 Hz, 2H), 7.48-7.59 (m, 2H), 6.95 (s, 1H), 3.03 (d, J=6.64 Hz, 2H), 2.82 (br s, 2H), 2.26 (s, 2H), 1.99 (br s, 1H), 1.78 (br s, 2H), 1.55 (br s, 2H), 1.33 (br s, 2H), 0.89-1.02 (m, 3H); 19F NMR (400 MHz, DMSO-d6) δ (ppm)-59.9 ppm; MS (ESI): m/z 404.2 [M+1]+.