2-cyclopropyl-4-methoxy-1-(phenylmethyl)-1H-indole → 2-cyclopropyl-4-hydroxy-1-(phenylmethyl)-1H-indole
Reaction equation
[CH:1]1([C:4]2[N:5]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:6]3[C:11]([CH:12]=2)=[C:10]([O:13]C)[CH:9]=[CH:8][CH:7]=3)[CH2:3][CH2:2]1.B(Br)(Br)Br.C(Cl)Cl>>[CH:1]1([C:4]2[N:5]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:6]3[C:11]([CH:12]=2)=[C:10]([OH:13])[CH:9]=[CH:8][CH:7]=3)[CH2:2][CH2:3]1Participants
3
Procedure
By the method used in Example 1, Part D, 630 g (2.3 mmol) of 2-cyclopropyl-4-methoxy-1-(phenylmethyl)-1H-indole was O-demethylated by treating it with 9 mL of 1M BBr3 /CH2Cl2. The crude product was chromatographed on silica gel and eluted with 20% EtOAc/hexane to give 316 mg (52% yield) of 2-cyclopropyl-4-hydroxy-1-(phenylmethyl)-1H-indole as an oil.
Workup
- customThe crude product was chromatographed on silica gel
- washeluted with 20% EtOAc/hexane