P(Br)(Br)[Br:2].[C:5]([N:12]1[C:20]2[C:15](=[C:16]([CH2:21]O)[CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1)([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].C([O-])(O)=O.[Na+]>CCOCC.C(Cl)Cl>[Br:2][CH2:21][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:15]=1[CH:14]=[CH:13][N:12]2[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]PBr3 (2.4 mL. 25.8 mmol) was added dropwise at 0° C. under nitrogen to a stirred solution of tert-butyl 4-(hydroxymethyl) 1H-1-indolecarboxylate 6 (6.0 g, 24.3 mmol) in ether (80 mL) and CH2Cl2 (20 mL) under nitrogen. The reaction was completed 30 minutes after the addition. The mixture was poured into a cold aqueous NaHCO3 solution (100 mL) and extracted with ethyl acetate (3×80 mL). The combined extract was washed sequentially with water (80 mL), and brine (80 mL), then dried (MgSO4), filtered, and finally concentrated to provide tert-butyl 4-(bromomethyl)-1H-1-indolecarboxylate 7 (6.3 g, 84%) as an oil which was immediately taken to the next step.
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