Reaction SMILES: [NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].I[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>[Cu](I)I.N[C@@H]1CCCC[C@H]1N.O1CCOCC1>[C:19]1([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][N:8]=3)[CH:3]=[CH:2]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
Reactant: Ic1ccccc1
Reactant: c1cnc2[nH]ccc2c1
Agent: I[Cu]I
Agent: N[C@@H]1CCCC[C@H]1N
Agent: O=P([O-])([O-])[O-]
Solvent: C1COCCO1
Product: c1ccc(-n2ccc3cccnc32)cc1
Temperature: 110 °C
Reaction time: 24 h
Yield: 100.1 %

Procedure:
To a mixture of 7-azaindole (550 mg, 4.66 mmol), copper iodide (7.4 mg, 0.038 mmol) and potassium phosphate (1.74 g, 8.18 mmol) under a N2 atmosphere is added racemic trans-1,2-diaminocyclohexane (0.046 mL, 0.38 mmol), iodobenzene (0.436 mL, 3.9 mmol) followed by anhydrous dioxane (5 mL). The resulting suspension is heated in an oil bath at 110° C. with magnetic stirring for 24 hours. The resulting mixture is filtered through a short pad of silica gel, washing the cake well with ethyl acetate. The filtrate is evaporated to leave a brown oil. The residue is purified by flash chromatography on a 10-gram silica gel cartridge by elution with heptane:ethyl acetate (4:1). Fractions containing the product are combined and the solvent evaporated, and further purified by flash chromatography on a 10-gram silica gel cartridge by elution with heptane:ethyl acetate (19:1). Clean fractions containing the product are combined and evaporated to give 758 mg of 1-phenyl-7-azaindole as a light brown oil (100% yield). 1H NMR (300 MHz, CDCl3): 8.37 (1H, dd), 7.97 (1H, dd), 7.76 (2H, d), 7.56-7.49 (3H, m), 7.35 (1H, t), 7.13 (1H, dd), 6.63 (1H, d). Step 2: 3,3-Dibromo-1-phenyl-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one: A solution of 1-phenyl-7-azaindole (325 mg, 1.68 mmol) in tert-butanol (12 mL) under N2 atmosphere is treated with pyridinium bromide perbromide (2.15 g, 6.71 mmol) portion wise over 3.5 hours, with occasional gentle heating on a hot plate to prevent freezing of the reaction mixture. Part of the way through the addition the mixture crashes out to give a thick orange suspension. The reaction is stirred for an additional 2.5 hours. The reaction mixture is evaporated and the residue is partitioned between water and ethyl acetate. The ethyl acetate layer is separated and washed with 2 further portions of water and a portion of saturated brine, and is dried over magnesium sulfate. Filtering and evaporation gives a orange solid. The crude product is triturated with ether, and the resulting solid separated, and dried under vacuum to give 612 mg of 3,3-dibromo-1-phenyl-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one as an orange solid (99% yield). MS: m/e 367/369/371 (M+H), 389/391/393 (M+Na). 1H NMR (300 MHz, CDCl3): 8.24 (1H, dd), 7.94 (1H, dd), 7.51-7.60 (4H, m), 7.47 (1H, m), 7.18 (1H, dd). Step 3: 1-Phenyl-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one: 3,3-dibromo-1-phenyl-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (600 mg, 1.63 mmol) and 10% by weight palladium on activated charcoal (300 mg) are suspended in absolute ethanol (60 mL). This mixture is allowed to stir under a hydrogen atmosphere at atmospheric pressure for 17 hours. The reaction mixture is filtered through a pad of hiflo, washing the cake well with ethanol. Concentration of the filtrate gives crude 1-phenyl-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one as an orange brown solid. This material was used without any further purification. MS: m/e 211 (M+H), 443 (2M+Na). Step 4: 2-Chloro-1-phenyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde: An ice-acetone cooled solution of anhydrous dimethylformamide (0.71 mL, 9.17 mmol) and anhydrous dichloromethane (1 mL) under a N2 atmosphere is treated drop-wise with phosphorus oxychloride (0.69 mL, 7.42 mmol). The resulting yellowish mixture is continued to stir for 30 mins to give an opaque gel. Crude 1-phenyl-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one is added portion wise as a solid over 10 minutes to form a red mixture. Further dichloromethane (1 mL) is added followed by pyridine (0.45 mL, 5.56 mmol) to give a dark red mixture. The reaction is allowed to warm slowly to room temperature over 1 hour, and stirred at room temperature for 38 hours. The red reaction mixture is concentrated, and the residue is treated with phosphorus oxychloride (8 mL) and the mixture heated in an oil bath at 110° C. for 3 hours. After concentration of the red mixture, the residue is treated with ice water, and treated with saturated aqueous sodium hydrogen carbonate solution until the effervescence ceases. The mixture is extracted with 5 portions of dichloromethane, the combined extracts are dried over magnesium sulfate, filtered and evaporated to leave an orange solid. The residue is purified by flash chromatography on a 5-gram silica gel cartridge by elution with dichloromethane. Fractions containing the product are combined and the solvent evaporated, and after trituration with heptane gives 220 mg of 2-chloro-1-phenyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde as a fluffy pink solid (53% yield from 3,3-dibromo-1-phenyl-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one). MS: m/e 257/259 (M+H). 1H NMR (300 MHz, CDCl3): 10.24 (1H, s), 8.62 (1H, dd), 8.39 (1H, dd), 7.68-7.56 (3H, m), 7.49 (2H, d), 7.31 (1H, dd).