Boron tribromide → 2-ethyl-5-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamide
Reaction equation
[CH2:1]([C:3]1[N:4]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]2[C:10]([C:11]=1[CH2:12][C:13]([NH2:15])=[O:14])=[CH:9][C:8]([O:16]C)=[CH:7][CH:6]=2)[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([C:3]1[N:4]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:5]2[C:10]([C:11]=1[CH2:12][C:13]([NH2:15])=[O:14])=[CH:9][C:8]([OH:16])=[CH:7][CH:6]=2)[CH3:2]Participants
4
Procedure
2-Ethyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetamide (5.05 g, 15.7 mmol) and 47 mL of 1M BBr3 in 100 mL of methylene chloride was reacted as described in Example 56, Part C to give a product that was chromatographed on silica gel eluting with EtOAc to give 3.64 g (75% yield) of 2-ethyl-5-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamide as a yellow foam.