Reaction SMILES: [H-].[Na+].[N+:3]([C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[CH:11][NH:12]2)=[CH:8][CH:7]=1)([O-:5])=[O:4].[Cl:15][CH2:16][CH2:17][CH2:18][CH2:19]I.N1C2C(=CC=CC=2)C=C1>CN(C=O)C.ClCCCC>[Cl:15][CH2:16][CH2:17][CH2:18][CH2:19][N:12]1[C:13]2[C:9](=[CH:8][CH:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:14]=2)[CH:10]=[CH:11]1
Reactant: ClCCCCI
Reactant: O=[N+]([O-])c1ccc2cc[nH]c2c1
Agent: [H-]
Agent: [Na+]
Agent: c1ccc2[nH]ccc2c1
Solvent: CN(C)C=O
Solvent: CCCCCl
Product: O=[N+]([O-])c1ccc2ccn(CCCCCl)c2c1
Temperature: 0 °C
Reaction time: 0.08 h
Yield: 97.5 %

Procedure:
To sodium hydride (0.987 g, 24.68 mmol) in a 100 mL argon-purged flask fitted with a stir bar and an Argon atmosphere was added anhydrous DMF (10 mL) and the mixture was cooled to 0° C. in an ice bath. A solution of 6-nitroindole (6) (1.00 g, 6.17 mmol) in DMF (10 mL) was added slowly to the NaH mixture and after addition was complete the ice bath was removed and the reaction stirred at room temperature for ˜5 min. In a second oven dried argon purged flask fitted with a stir bar was charged 1-Chloro-4-iodo-butane (2.26 mL, 18.51 mmol) and DMF (10 mL). The indole solution was added via cannula to the chlorobutane solution over a period of 10 min and the mixture was stirred at RT. After 20 min, the reaction was placed in an ice bath and quenched with brine (10 mL). The reaction was diluted with ethyl acetate and water and transferred to a separatory funnel. The organic layer was separated and the aqueous layer further extracted with EtOAc. The combined organics were washed with brine, dried with magnesium sulfate, filtered and concentrated to afford a brown oil. The crude product was purified via chromatography on silica gel (20% Ethyl acetate/80% Hexanes) to afford compound 165 (1.52 g, 97.6% yield);1 H-NMR (DMSO-d6) δ 8.57 (d, 1H, J=1.8), 7.93-7.88 (m, 1H), 7.84 (d, 1H, J=3.0), 7.75-7.72 (m, 1H), 6.67 (d, 1H, J=3.0), 4.39 (t, 2H, J=7.0), 3.66 (t, 2H, J=6.6), 1.95-1.82 (m, 2H), 1.73-1.64 (m, 2H); MS (ESI+): 253 (M+1, 100%). Preparation of compound 166: To an over dried, Argon purged 50 mL flask fitted with stir bar and condenser, 1H-Imidazole (0.673 g, 9.893 mmol), potassium iodide (1.642 g, 9.893 mmol) and potassium carbonate (1.367 g, 9.893 mmol) were added as solids. 1-(4-chlorobutyl)-6-nitro-1H-indole (compound 165, 0.250 g, 0.989 mmol) in a solution of acetonitrile (5 mL) was charged to the flask and stirring began. Mixture was heated at 50° C. for 16 hours then heated to reflux for 4 hours. The reaction was cooled to room temperature and diluted with dichloromethane (10 mL) and filtered through a pad of celite. The pad was washed further with dichloromethane and the solution was concentrated to afford a crude yellow solid. The product was purified by silica gel column chromatography using a solvent system of (5% 2M NH3 in methanol/95% dichloromethane) to yield a yellow residue, compound 166 (182 mg, 64.7% yield); 1H-NMR (DMSO-d6) δ 8.54 (d, 1H, J=1.5), 7.94-7.88 (m, 1H), 7.81 (d, 1H, J=3.0), 7.74-7.72 (m, 1H), 7.59 (s, 1H), 7.12 (s, 1H), 6.86 (s, 1H), 6.66 (d, 1H, J=3.0), 4.35 (t, 2H, J=6.4), 3.97 (t, 2H, J=6.4), 1.76-1.61 (m, 4H); MS (ESI+): 307 (M+Na, 100%). Preparation of compound 168: 1-(4-(1H-imidazol-1-yl)butyl)-6-nitro-1H-indole (compound 166, 145 mg, 0.510 mmol) was dissolved in anhydrous ethanol (7 mL) in a dry argon purged flask. Palladium, 10 wt % on activated carbon (54.2 mg, 0.051 mmol) is quickly added and the atmosphere from the flask evacuated by vacuum pump and replaced with hydrogen from a balloon. The atmosphere is evacuated from the flask and replaced with hydrogen twice more and the mixture stirred under a hydrogen atmosphere at room temperature. After 3 hours, thin layer chromatography in a solvent system of (10% 2M NH3 in methanol/90% dichloromethane) shows complete conversion to compound 167, 1-(4-(1H-imidazol-1-yl)butyl)-1H-indol-6-amine, which is utilized without isolation. The mixture is filtered through a pad of celite to remove insolubles, the pad washed with anhydrous ethanol (7 mL) and the ethanolic solution of the amine 167 is charged to a small, argon purged flask fitted with a magnetic stir bar. Thiophene-2-carboximidothioic acid methyl ester hydroiodide (189.1 mg, 0.663 mmol) is added to the flask and the reaction was stirred under Ar at ambient temperature for 20 hours, at which time the solution was diluted with diethyl ether (100 ml) resulting in the formation of a sticky solid which could not be isolated via filtration. As a result the product was washed off the funnel with methanol, combined with the filtrate and solvents evaporated to leave a crude residue. The residue was partitioned between H2O and ethyl acetate and 3M sodium hydroxide solution added to adjust pH to 9. The mixture was transferred to a separatory funnel and the organic layer collected. The aqueous layer was further extracted with ethyl acetate and the combined organic layers were washed with brine, dried over magnesium sulfate, filtered, concentrated and the residue purified via chromatography on silica gel (2.5% 2M NH3 in methanol/97.5% dichloromethane) to yield yellow solid, compound 168 (101 mg, 54.5% yield); 1H-NMR (DMSO-d6) δ 7.74 (d, 1H, J=3.0), 7.60 (d, 1H, J=5.2), 7.56 (s, 1H), 7.45 (d, 1H, J=8.3), 7.21 (d, 1H, J=3.0), 7.13-7.06 (m, 2H), 6.92 (s, 1H), 6.85 (s, 1H), 6.59 (d, 1H, J=8.0), 6.42-6.30 (br, 2×m, 3H), 4.17-4.06 (m, 2H), 3.99-3.92 (m, 2H), 1.75-1.58 (m, 4H); MS (ESI+): 364 (M+1, 100%).