Reaction SMILES: Br[C:2]1[C:3]2[N:4]([N:8]=[C:9]([Cl:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:12][CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]([CH3:26])[S:22]([CH3:25])(=[O:24])=[O:23])[CH3:14]>>[Cl:11][C:9]1[N:10]=[C:3]2[C:2]([NH:12][CH:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:21]([CH3:26])[S:22]([CH3:25])(=[O:24])=[O:23])[CH3:14])=[CH:7][CH:6]=[CH:5][N:4]2[N:8]=1
Reactant: Clc1nc2c(Br)cccn2n1
Reactant: CC(N)c1ccccc1N(C)S(C)(=O)=O
Product: CC(Nc1cccn2nc(Cl)nc12)c1ccccc1N(C)S(C)(=O)=O

Procedure:
197 a) A round bottom flask was charged with (2-nitro-phenyl)-acetic acid methyl ester (4.22 g, 21.6 mmol) (prepared as described in Organic Letters, 2009, 11, 1345-1348), iodomethane (2.8 mL, 45 mmol) and dry dimethyl sulfoxide (20 mL). Cesium carbonate (18 g, 56 mmol) was added and the mixture was stirred at room temperature under an atmosphere of nitrogen for 18 hours. Water (50 mL) was added and the mixture was extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with water (2×30 mL), saturated aqueous sodium chloride (30 mL), dried over magnesium sulfate, filtered and evaporated. 2-(2-Nitro-phenyl)-propionic acid methyl ester was isolated as a red oil (3.24 g, 71%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.93 (d, J=8.1 Hz, 1H), 7.60 (t, J=7.6 Hz, 1H), 7.49 (d, J=7.8 Hz, 1H), 7.43 (t, J=7.7 Hz, 1H), 4.32 (q, J=7.0 Hz, 1H), 3.67 (s, 3H), 1.61 (d, J=7.0 Hz, 3H). MS=232 (MH)+. 197 b) 2-(2-Amino-phenyl)-propionic acid methyl ester was prepared from 2-(2-nitro-phenyl)-propionic acid methyl ester (1.22 g, 5.83 mmol) in a manner analogous to Example 111a. Product isolated as a crude tan oil (1.0 g, 96%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.16 (d, J=7.6 Hz, 1H), 7.08 (t, J=7.6 Hz, 1H), 6.79 (t, J=7.5 Hz, 1H), 6.70 (d, J=7.9 Hz, 1H), 3.99 (br s, 2H), 3.82 (q, J=7.2 Hz, 1H), 3.67 (s, 3H), 1.54 (d, J=7.2 Hz, 3H). MS=148 [(M-OCH3)]+. 197 c) 2-(2-Methanesulfonylamino-phenyl)-propionic acid methyl ester was prepared from 2-(2-Amino-phenyl)-propionic acid methyl ester (1.0 g, 5.6 mmol) in a manner analogous to Example 189b. Product isolated as a yellow viscous oil (0.843 g, 59%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.52 (d, J=7.7 Hz, 1H), 7.46 (s, 1H), 7.37-7.21 (m, 3H), 4.05 (q, J=7.1 Hz, 1H), 3.69 (s, 3H), 3.07 (s, 3H), 1.58 (d, J=7.1 Hz, 1H). MS=280 (M+Na)+. 197 d) 2-[2-(Methanesulfonyl-methyl-amino)-phenyl]-propionic acid methyl ester was prepared from 2-(2-methanesulfonylamino-phenyl)-propionic acid methyl ester (0.843 g, 3.28 mmol) in a manner analogous to Example 189c. Product isolated as a pale yellow solid (0.880 g, 99%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.46 (d, J=7.6 Hz, 1H), 7.40-7.26 (m, 3H), 4.47-4.30 (m, 1H), 3.70-3.63 (m, 3H), 3.28-3.22 (m, 3H), 2.99 (s, 3H), 1.56-1.44 (m, 3H). MS=294 (M+Na)+. 197 e) To a solution of 2-[2-(Methanesulfonyl-methyl-amino)-phenyl]-propionic acid methyl ester (0.880 g, 3.24 mmol) in methanol (15 mL) and water (10 mL) was added lithium hydroxide monohydrate (0.687 g, 16.4 mmol). The mixture was stirred at room temperature for 24 hours then extracted with dichloromethane (3×30 mL). The combined organic layers were dried over magnesium sulfate, filtered and evaporated. 2-[2-(Methanesulfonyl-methyl-amino)-phenyl]-propionic acid was isolated as a yellow viscous oil (0.755 g, 91%). 1H NMR (400 MHz, CDCl3, δ, ppm): 9.73 (br s, 1H), 7.51-7.28 (m, 4H), 4.53-4.34 (m, 1H), 3.32-3.25 (m, 3H), 3.05-2.98 (m, 3H), 1.56-1.40 (m, 3H). MS=280 (M+Na)+. 197 f) To a solution of 2-[2-(methanesulfonyl-methyl-amino)-phenyl]-propionic acid (0.755 g, 2.93 mmol) and diphenylphosphonic azide (0.95 mL, 4.4 mmol) in dichloromethane (25 mL) was added triethylamine (0.65 mL, 4.7 mmol). The mixture was stirred at room temperature for 24 hours then cooled to 5° C. and 2N Hydrochloric acid (30 mL) was added and the mixture stirred for 10 minutes. The layers were separated and the aqueous was washed with dichloromethane (2×10 mL). The combined organic layers were dried over magnesium sulfate, filtered and evaporated. The residue dissolved in tert-butyl alcohol (10 mL, 100 mmol) and heated at 80° C. for 18 hours. The volatiles were evaporated and the residue was dissolved in ethyl acetate (50 mL). The organic layer was washed with saturated aqueous sodium carbonate (30 mL), dried over magnesium sulfate, filtered and evaporated. The residue was dissolved in dichloromethane (5 mL) and trifluoroacetic acid (2 mL, 20 mmol) was added. The mixture was stirred at room temperature overnight. The volatiles were evaporated. The residue was dissolved in ethyl acetate (50 mL) and was extracted with 2N Hydrochloric acid (3×20 mL). The combined acidic aqueous layers were basified with 2M sodium hydroxide to pH 10. The basic aqueous layer was extracted with dichloromethane (3×20 mL). The combined organic layers were dried over magnesium sulfate, filtered and evaporated. N-[2-(1-Amino-ethyl)-phenyl]-N-methyl-methanesulfonamide was isolated as a crude tan viscous oil (0.380 g, 56%). 197 g) N-{2-[1-(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-ethyl]-phenyl}-N-methyl-methanesulfonamide was prepared from 8-bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridine (350.0 mg, 1.506 mmol) and N-[2-(1-amino-ethyl)-phenyl]-N-methyl-methanesulfonamide (380.0 mg, 1.664 mmol) in a manner analogous to Example 2d. Product isolated as a yellow foam (0.315 g, 55%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.83-7.79 (m, 1H), 7.62-7.25 (m, 4H), 6.85-6.71 (m, 1H), 6.61-6.43 (m, 1H), 5.42-6.13 (m, 2H), 3.35-3.26 (m, 3H), 3.08-3.00 (m, 3H), 1.70-1.53 (m, 3H). MS=402 (M+Na)+. 197 h) N-Methyl-N-[2-(1-{2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino}-ethyl)-phenyl]-methanesulfonamide was prepared from N-{2-[1-(2-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-ethyl]-phenyl}-N-methyl-methanesulfonamide (75.0 mg, 0.197 mmol) and 4-(4-methyl-piperazin-1-yl)-phenylamine (42.0 mg, 0.220 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (18.0 mg, 0.0329 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a pale yellow solid (0.008 g, 8%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.77-7.25 (m, 8H), 7.00-6.93 (m, 2H), 6.65-6.30 (m, 3H), 5.40-5.24 (m, 1H), 5.00-4.91 (m, 1H), 3.35-3.29 (m, 3H), 3.19-3.13 (m, 4H), 3.07-3.01 (m, 3H), 2.63-2.58 (m, 4H), 2.36 (s, 3H), 1.72-1.55 (m, 3H). MS=535 (MH)+.