Reaction SMILES: C([O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[CH:8]2)C=C.[H-].[Na+].I[CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19].N1C2[C:25](=CC=CC=2)[CH:24]=[CH:23]1.C1(OC2C=CC=CC=2)C=CC=CC=1>[Pd].C(OCC)(=O)C.CN(C=O)C>[CH3:17][C:18]([CH3:21])([CH3:20])[CH2:19][N:10]1[C:11]2[C:7](=[C:6]([CH2:23][CH2:24][CH3:25])[C:5]([OH:4])=[CH:13][CH:12]=2)[CH:8]=[CH:9]1
Reactant: CC(C)(C)CI
Reactant: C=CCOc1ccc2[nH]ccc2c1
Reactant: c1ccc2[nH]ccc2c1
Agent: [Pd]
Agent: [H-]
Agent: [Na+]
Solvent: CCOC(C)=O
Solvent: CN(C)C=O
Solvent: c1ccc(Oc2ccccc2)cc1
Product: CCCc1c(O)ccc2c1ccn2CC(C)(C)C
Temperature: 25 °C
Reaction time: 15 h

Procedure:
5-(Allyloxy)-1H-indole (8.0 g, 46 mmol) was added in 1 g portions to a mixture of NaH (3.5 g, 60 wt %, 88 mmol) and DMF (80 ml) at 0° C. under N2. The reaction was allowed to warm to rt and then 1-Iodo-2,2-dimethylpropane (20 mL, 0.15 mol) was added. After stirring for 15 h, the mixture was heated at 70° C. for 8 h and then allowed to cool to rt. The reaction mixture was concentrated, diluted with water (200 mL), and extracted with ethyl acetate (100 mL×2). The combined organic extracts were dried (MgSO4), filtered, and concentrated to give clear oil. MS (ESI): 244.1 (M+H). A solution of the above indole and diphenyl ether (40 mL) was heated at 190° C. for 4 h under N2 and then allowed to cool to rt. The resulting solution was purified by silica gel chromatography (hexanes:ethyl acetate—1:0→2:1) to give an off-white solid. MS (ESI): 244.1 (M+H). The above indole, Pd/C (1.8 g, 10 wt %, 1.7 mmol Pd), and ethyl acetate (50 mL) were stirred vigorously under an atmosphere of H2 for 3 h. The reaction mixture was filtered through Celite with ethyl acetate (100 mL) and concentrated to give 1-(2,2-dimethylpropyl)-4-propyl-1H-indol-5-ol. MS (ESI): 246.0 (M+H). A mixture of the above indole (3.0 g, 12.2 mmol), 4-(4-bromobutoxy)benzonitrile (3.4 g, 13.4 mmol), K2CO3 (4 g, 29 mmol), and DMF (15 mL) was heated at 90° C. under N2-acetone can be used in place of DMF, but longer reaction times are required. After 22 h, a second aliquot of both 4-(4-bromobutoxy)benzonitrile and K2CO3 were added. After an additional 10 h, a third aliquot of both 4-(4-bromobutoxy)benzonitrile and K2CO3 were added. After an additional 12 h, the reaction was allowed to cool to rt. The resulting mixture was filtered through Celite with chloroform (100 mL), concentrated, and purified by silica gel chromatography (hexanes:ethyl acetate—1:0→3:2) to give a light brown solid. MS (ESI): 419.2 (M+H). A solution of the above indole (3.0 g, 7.2 mmol), trimethylsilylazide (10 mL, 75 mmol), dibutyltin oxide (360 mg, 1.5 mmol), and toluene (30 mL) was heated at reflux for 14 h under N2 and then allowed to cool to rt. The reaction mixture was poured onto silica, washed with hexanes (300 mL), and then eluted with CH3OH:CHCl3 (1:4; 500 mL). The collected eluent was concentrated and purified by silica gel chromatography (hexanes:ethyl acetate—7:3→0:1) or reverse-phase HPLC to give a white solid. 1H NMR (500 MHz, DMSO) δ 7.97 (d, 2H), 7.24 (d, 1H), 7.21 (d, 1H), 7.19 (d, 2H), 6.88 (d, 1H), 6.37 (d, 1H), 4.16 (t, 2H), 4.02 (t, 2H), 3.90 (s, 2H), 2.77 (t, 2H), 2.00-1.88 (m, 4H), 1.61-1.55 (m, 2H), 0.92 (s, 9H), 0.90 (t, 3H). MS (ESI): 462.1 (M+H).