alpha-Bromo-o-fluorotoluene → 2,3-Dibromo-1-(2-fluoro-benzyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642506Notes

Reaction equation

HRID 642506 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:25])=[C:8]2[C:14]([Br:15])=[C:13]([Br:16])[N:12]([CH2:17][C:18]3[CH:23]=[CH:22][C:21](F)=[CH:20][CH:19]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].C(OC(C1C=CNC=1C)=O)C.[F:37]C1C=CC=CC=1CBr>>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:25])=[C:8]2[C:14]([Br:15])=[C:13]([Br:16])[N:12]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:37])[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 67968alpha-Bromo-o-fluorotolueneHCID 136747Ethyl 2-methyl-3-pyrrolecarboxylateHCID 598558191h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,2,3-dibromo-1-[(4-fluorophenyl)methyl]-4-hydroxy-,ethyl ester

Product 1

HCID 684266692,3-Dibromo-1-(2-fluoro-benzyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Procedure

Prepared similarly according to a reaction sequence in Example 117 steps (a), (b), (c) and (d) for the synthesis of 2,3-dibromo-1-(4-fluoro-benzyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester starting from 2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester, 2-fluorobenzyl bromide. The title compound, ESI MS (m/z): 471 (M+H)+.

Workup

  1. customPrepared similarly

Sources & evidence

ORD record
ord-e8db5c01f78b475b90cb54d48fa5a404
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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