Benzoyl Peroxide → 2,3,7-Tribromo-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642440Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:23])=[C:8]2[C:14]([Br:15])=[C:13]([Br:16])[N:12]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].C1C(=O)N([Br:31])C(=O)C1.C(OOC(C1C=CC=CC=1)=O)(C1C=CC=CC=1)=O>>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:23])=[C:8]2[C:14]([Br:15])=[C:13]([Br:16])[N:12]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:9]2=[C:10]([Br:31])[N:11]=1)=[O:5])[CH3:2]

Participants

Reactant 3

HCID 7187Benzoyl Peroxide

HCID 67184N-bromobutanimide

HCID 684263992,3-dibromo-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 866173682,3,7-Tribromo-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Procedure

Prepared in analogy to that of Example 103(a) from 2,3-dibromo-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester, NBS and BzOOBz. The title compound, ESI MS (m/z): 517 (M+H)+.

Sources & evidence

ORD record: ord-386c92b79bb84453bf05d419555ad518
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696223B2

Reaction notes

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