Cl[CH2:2][CH2:3][CH2:4][S:5]([CH3:8])(=[O:7])=[O:6].[NH:9]1[C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:18])[C:12]=2[CH:11]=[CH:10]1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:8][S:5]([CH2:4][CH2:3][CH2:2][O:18][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:12]=1[CH:11]=[CH:10][NH:9]2)(=[O:7])=[O:6]1-Chloro-3-(methanesulfonyl)-propane (160 g) was added to 1H-indol-4-ol (108.77 g) in 1 L MeCN, and 338 g K2CO3 and 13.36 g KI were added. The reaction mixture was stirred overnight at 80° C., then cooled and filtered through celite. The filtrate was vacuum distilled and solvent replaced with DCM (700 mL). The mixture was filtered, and the solvent removed in vacuo and replaced with MeOH (600 mL). The solvent was partially removed in vacuo at 40° C. and crystallization occurred. After cooling, additional MeOH was added and the slurry was filtered. The collected solid was rinsed with cold MeOH and dried overnight at 35° C. in vacuo under N2 to provide 4-(3-methanesulfonyl-propoxy)-1H-indole (82%).
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