Boron tribromide → HCID 10804743, compound

HRID 1069631Notes

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])=[C:9]([O:16]C)[CH:8]=[CH:7][CH:6]=2)[CH3:2].B(Br)(Br)Br>>[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])=[C:9]([OH:16])[CH:8]=[CH:7][CH:6]=2)[CH3:2]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 10853288HCID 10853288, compound

Product 1

HCID 10804743HCID 10804743, compound

Procedure

2-Ethyl-4-methoxy-1-(phenylmethyl)-1H-indole-3-acetamide (483 mg, 1.5 mmol) and 6 mL of BBr3 were reacted as described in Example 56, Part C, to give after chromatography on silica gel (eluted with ethyl acetate) 156 mg (34% yield) of 2-ethyl-4-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamide.

Sources & evidence

ORD record: ord-df567de9f0ea4bdb86d9b19656064beb
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06252084B1

Reaction notes

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