[H-].[Na+].[I:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=2)[NH:6][CH:5]=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.O>C1COCC1>[I:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=2)[N:6]([S:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=2)(=[O:25])=[O:24])[CH:5]=1NaH (60% w/w in mineral oil; 0.532 g, 13.30 mmol) was added (portionwise, over 2 min) to a solution of methyl 3-iodo-1H-indole-5-carboxylate (3.64 g, 12.09 mmol) in THF (30 mL) at 0° C., and the resulting mixture was stirred at 0° C. for 5 min. p-Toluenesulfonyl chloride (2.54 g, 13.30 mmol) was then added (portionwise, over 2 min), and the resulting mixture was stirred at 0° C. for 1 h. H2O (50 mL) was carefully added to the mixture at 0° C. and the reaction was warmed to 25° C. THF was removed in vacuo, and the resulting tan mixture was vacuum filtered. The collected solid was washed with H2O (150 mL) and dried in vacuo to provide crude methyl 3-iodo-1-tosyl-1H-indole-5-carboxylate (5.94 g) as a tan solid: MS (ESI, pos. ion) m/z: 455.9 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 8.03-8.11 (2H, m), 7.97-8.02 (1H, m), 7.79 (2H, d, J=8.2 Hz), 7.75 (1H, s), 7.26 (2H, d, J=8.2 Hz), 3.94 (3H, s), 2.36 (3H, s).
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