Reaction SMILES: Cl[C:2]1[N:24]=[C:5]2[C:6]([NH:10][CH2:11][C:12]3[C:13]([N:18]([CH3:23])[S:19]([CH3:22])(=[O:21])=[O:20])=[N:14][CH:15]=[CH:16][CH:17]=3)=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:25][N:26]1[CH2:34][C:33]2[C:28](=[CH:29][CH:30]=[C:31]([NH2:35])[CH:32]=2)[CH2:27]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH3:23][N:18]([C:13]1[C:12]([CH2:11][NH:10][C:6]2[C:5]3[N:4]([N:3]=[C:2]([NH:35][C:31]4[CH:32]=[C:33]5[C:28](=[CH:29][CH:30]=4)[CH2:27][N:26]([CH3:25])[CH2:34]5)[N:24]=3)[CH:9]=[CH:8][CH:7]=2)=[CH:17][CH:16]=[CH:15][N:14]=1)[S:19]([CH3:22])(=[O:21])=[O:20]
Reactant: CN(c1ncccc1CNc1cccn2nc(Cl)nc12)S(C)(=O)=O
Reactant: CN1Cc2ccc(N)cc2C1
Agent: c1ccc(P(C2CCCCC2)C2CCCCC2)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c1
Product: CN1Cc2ccc(Nc3nc4c(NCc5cccnc5N(C)S(C)(=O)=O)cccn4n3)cc2C1

Procedure:
To a cooled solution of 2,3-dihydro-1H-isoindole (8.80 g, 73.8 mmol) in acetonitrile (80 mL) at −10° C. was added trifluoroacetic anhydride (36.1 mL, 255 mmol) dropwise. Potassium nitrate (7.50 g, 74.2 mmol) was added in one portion to the stirred mixture. The mixture was stirred at −10° C. for 1 hour. To the mixture was added saturated aqueous sodium bicarbonate (100 mL) slowly. Vigorous gas evolution was noted. The mixture was stirred for 1 hour and allowed to warm to room temperature. The mixture was basified with saturated aqueous sodium carbonate (100 mL). The thick suspension was filtered. The solid was washed with water (200 mL), dissolved in dichloromethane (300 mL) and separated. The organic layer was dried over magnesium sulfate, filtered and evaporated to a tan solid (17.97 g). The material was purified via flash chromatography using an ISCO automated purification apparatus (silica gel column and 10%→100% Ethyl Acetate:Hexane). 2,2,2-Trifluoro-1-(5-nitro-1,3-dihydro-isoindol-2-yl)-ethanone was isolated as a crude orange solid (16.8 g, 85%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.28-8.23 (m, 1H), 8.20 (d, J=17.6 Hz, 1H), 7.50 (dd, J=21.7, 8.40 Hz, 1H), 5.14 (s, 2H), 5.02 (s, 2H). MS=261 (MH)+. 166 b) To a solution of 2,2,2-Trifluoro-1-(5-nitro-1,3-dihydro-isoindol-2-yl)-ethanone (16.8 g, 64.6 mmol) in acetonitrile (300 mL, 6000 mmol) at 0° C. was added 33% aqueous sodium hydroxide (100 mL) slowly with vigorous stirring. The mixture was stirred at 0° C. for 1 hour then allowed to warm to room temperature for 4 hours. The reaction mixture was transferred to a separation funnel and the layers separated. The organic layer was dried over sodium sulfate, filtered and evaporated to a dark oily material. The residue was dissolved in dichloromethane (500 mL) and separated. The organic layer was dried over magnesium sulfate, filtered and evaporated to yield a dark viscous oil (12 g) and was placed under high vacuum for 4 hours. Crude 5-Nitro-2,3-dihydro-1H-isoindole was isolated as a dark brown waxy solid (10 g, 94%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.16-8.09 (m, 2H), 7.39 (d, J=8.1 Hz, 1H), 4.36 (s, 4H). MS=165 (MH)+. 166 c) To a stirred solution of crude 5-nitro-2,3-dihydro-1H-isoindole (9.0 g, 55 mmol) and 4-dimethylaminopyridine (0.33 g, 2.7 mmol) in N,N-dimethylformamide (50 mL) was added di-tert-Butyldicarbonate (14 mL, 6.0.0 mmol) and the mixture was stirred for 18 hours at room temperature. To the mixture was added water (150 mL) and the mixture was stirred vigorously for 30 minutes. The resulting precipitate was filtered, rinsed with water and dried by suction. Crude 5-nitro-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester was isolated as brown solid (7.88 g, 54%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.20-8.09 (m, 2H), 7.41 (dd, J=21.1, 8.6 Hz, 1H), 4.77 (s, 2H), 4.74 (s, 2H), 1.53 (s, 9H). MS=287 (M+Na)+. 166 d) 5-Amino-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester was prepared from crude 5-nitro-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (3.0 g, 11 mmol) in a manner analogous to Example 111a. Product isolated as a brown viscous oil (2.21 g, 83%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.01 (dd, J=19.7, 8.1 Hz, 1H), 6.62-6.52 (m, 2H), 4.61-4.51 (m, 4H), 3.66 (br s, 2H), 1.51 (s, 9H). MS=235 (MH)+. 166 e) To a cooled solution of 2.0 M of lithium tetrahydroborate in tetrahydrofuran (13 mL, 26 mmol) at 5° C. was added dropwise a solution of 5-amino-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (1.0 g, 4.3 mmol) in tetrahydrofuran (50 mL). Gas evolution was noted. The mixture was stirred for 1 hour at 5° C. then warmed to room temperature and stirred for 24 hours. The mixture was cooled to 5° C. in a ice/water bath and the reaction was quenched by addition of sodium sulfate decahydrate (3 g). Gas evolution noted. The mixture was stirred for 2 hours at room temperature. The suspension was filtered through a plug of diatomaceous earth and rinsed with tetrahydrofuran. The filtrate was dried over magnesium sulfate, filtered and evaporated. The residue was purified via flash chromatography (silica gel column and 0%→20% methanol: dichloromethane). 2-Methyl-2,3-dihydro-1H-isoindol-5-ylamine was isolated as an orange solid (0.271 g, 43%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 6.82 (d, J=7.9 Hz, 1H), 6.41 (s, 1H), 6.37 (d, J=8.1 Hz, 1H), 4.86 (br s, 2H), 3.64 (s, 2H), 3.62 (s, 2H), 2.42 (s, 3H). MS=149 (MH)+. 166 f) N-Methyl-N-(3-{[2-(2-methyl-2,3-dihydro-1H-isoindol-5-ylamino)-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino]-methyl}-pyridin-2-yl)-methanesulfonamide was prepared from N-{3-[(2-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-methyl]-pyridin-2-yl}-N-methyl-methanesulfonamide (75.0 mg, 0.204 mmol) and 2-methyl-2,3-dihydro-1H-isoindol-5-ylamine (34.0 mg, 0.229 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (25.0 mg, 0.0457 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as tan foam (0.048 g, 49%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.41 (d, J=3.6 Hz, 1H), 7.87-7.81 (m, 2H), 7.53 (s, 1H), 7.33-7.25 (m, 2H), 7.14 (d, J=8.1 Hz, 1H), 6.72 (s, 1H), 6.66 (t, J=7.4 Hz, 1H), 6.30 (d, J=7.6 Hz, 1H), 5.33-5.29 (m, 1H), 4.77 (d, J=6.2 Hz, 2H), 3.94 (s, 2H), 3.88 (s, 2H), 3.32 (s, 3H), 3.09 (s, 3H), 2.60 (s, 3H). MS=479 (MH)+.