Reaction SMILES: Cl[C:2]1[N:20]=[C:5]2[C:6]([C:10]3[CH:15]=[CH:14][C:13]([P:16]([CH3:19])([CH3:18])=[O:17])=[CH:12][CH:11]=3)=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:21][S:22]([CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][CH:30]([C:33]2[CH:34]=[C:35]([NH2:39])[CH:36]=[CH:37][CH:38]=2)[CH2:29][CH2:28]1)(=[O:24])=[O:23].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH3:18][P:16]([CH3:19])([C:13]1[CH:14]=[CH:15][C:10]([C:6]2[C:5]3[N:4]([N:3]=[C:2]([NH:39][C:35]4[CH:36]=[CH:37][CH:38]=[C:33]([CH:30]5[CH2:31][CH2:32][N:27]([CH2:26][CH2:25][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:28][CH2:29]5)[CH:34]=4)[N:20]=3)[CH:9]=[CH:8][CH:7]=2)=[CH:11][CH:12]=1)=[O:17]
Reactant: CP(C)(=O)c1ccc(-c2cccn3nc(Cl)nc23)cc1
Reactant: CS(=O)(=O)CCN1CCC(c2cccc(N)c2)CC1
Agent: c1ccc(P(C2CCCCC2)C2CCCCC2)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c1
Product: CP(C)(=O)c1ccc(-c2cccn3nc(Nc4cccc(C5CCN(CCS(C)(=O)=O)CC5)c4)nc23)cc1

Procedure:
203 a) To a solution of 4-(3-nitro-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.50 g, 1.6 mmol) in dichloromethane (3 mL) was added trifluoroacetic acid (1.2 mL, 16 mmol). The mixture was stirred at room temperature for 2 hours then the volatiles were evaporated. The residue was dissolved in N,N-dimethylformamide (5 mL). Cesium carbonate (0.60 g, 1.8 mmol), sodium iodide (25.0 mg, 0.167 mmol) and 1-chloro-2-methanesulfonyl-ethane (0.26 g, 1.8 mmol) were added. The mixture was heated at 50° C. for 18 hours then cooled to room temperature and water (30 mL) was added. The mixture was extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with water (2×20 mL) and saturated aqueous sodium chloride (20 mL), dried over magnesium sulfate, filtered and evaporated. 1-(2-Methanesulfonyl-ethyl)-4-(3-nitro-phenyl)-1,2,3,6-tetrahydro-pyridine was isolated as an orange viscous oil (0.381 g, 75%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.23 (s, 1H), 8.11 (d, J=8.0 Hz, 1H), 7.70 (d, J=8.0 Hz, 1H), 7.50 (t, J=8.0 Hz, 1H), 6.23 (s, 1H), 3.27 (s, 2H), 3.23 (t, J=6.5 Hz, 2H), 3.07-3.01 (m, 5H), 2.82 (t, J=5.5 Hz, 2H), 2.61 (br s, 2H). MS=311 (MH)+. 203 b) 3-[1-(2-Methanesulfonyl-ethyl)-piperidin-4-yl]-phenylamine was prepared from 1-(2-methanesulfonyl-ethyl)-4-(3-nitro-phenyl)-1,2,3,6-tetrahydro-pyridine (0.38 g, 1.2 mmol) in a manner analogous to Example 111a. Product isolated as a yellow waxy solid (0.34 g, 98%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.09 (t, J=7.4 Hz, 1H), 6.61 (d, J=7.6 Hz, 1H), 6.56-6.52 (m, 2H), 3.62 (br s, 2H), 3.17 (t, J=6.4 Hz, 2H), 3.06 (s, 3H), 3.02 (d, J=10.6 Hz, 2H), 2.90 (t, J=6.3 Hz, 2H), 2.42 (t, J=12.2 Hz, 1H), 2.15 (t, J=11.4 Hz, 2H), 1.85 (d, J=12.8 Hz, 2H), 1.75-1.63 (m, 2H). MS=283 (MH)+. 203 c) {8-[4-(Dimethyl-phosphinoyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-{3-[1-(2-methanesulfonyl-ethyl)-piperidin-4-yl]-phenyl}-amine was prepared from 2-chloro-8-[4-(dimethyl-phosphinoyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridine (75.0 mg, 0.245 mmol) and 3-[1-(2-methanesulfonyl-ethyl)-piperidin-4-yl]-phenylamine (78.0 mg, 0.276 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (21.0 mg, 0.0384 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as an off-white solid (0.078 g, 58%). MP=243-245° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 8.47 (d, J=6.9 Hz, 1H), 8.16 (d, J=8.1 Hz, 2H), 7.92-7.85 (m, 2H), 7.64 (d, J=7.3 Hz, 1H), 7.51 (s, 1H), 7.40 (d, J=8.1 Hz, 1H), 7.29 (t, J=7.3 Hz, 1H), 7.01 (t, J=7.1 Hz, 1H), 6.89-6.84 (m, 2H), 3.23 (t, J=6.0 Hz, 2H), 3.11-3.05 (m, 5H), 2.93 (t, J=6.0 Hz, 2H), 2.56 (t, J=12.7 Hz, 1H), 2.21 (t, J=11.6 Hz, 2H), 1.94 (d, J=12.7 Hz, 2H), 1.84-1.71 (m, 8H). MS=552 (MH)+.