Ethyl 2-methyl-3-pyrrolecarboxylate → 2,3-Dibromo-4-hydroxy-1-(4-methoxy-benzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642471Notes

Reaction equation

HRID 642471 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].[CH2:26]([O:28]C(C1C=CNC=1C)=O)C.COC1C=CC(CBr)=CC=1>>[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]([O:28][CH3:26])=[CH:20][CH:19]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 136747Ethyl 2-methyl-3-pyrrolecarboxylateHCID 1650214-Methoxybenzyl bromideHCID 598558191h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,2,3-dibromo-1-[(4-fluorophenyl)methyl]-4-hydroxy-,ethyl ester

Product 1

HCID 684263822,3-Dibromo-4-hydroxy-1-(4-methoxy-benzyl)-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, 4-methoxybenzyl bromide. The title compound, ESI MS (m/z): 483 (M+H)+.

Workup

  1. customPrepared similarly

Sources & evidence

ORD record
ord-08bbd9295ec449dc8b38406802fd6efe
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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