N-bromobutanimide → 2,3,7-Tribromo-4-hydroxy-1-(4-methoxy-benzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642474Notes

Reaction equation

HRID 642474 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:26])=[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:24][CH3:25])=[CH:20][CH:19]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].C1C(=O)N([Br:34])C(=O)C1>CC#N>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:26])=[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:24][CH3:25])=[CH:20][CH:19]=3)[C:9]2=[C:10]([Br:34])[N:11]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 684263822,3-Dibromo-4-hydroxy-1-(4-methoxy-benzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 866173712,3,7-Tribromo-4-hydroxy-1-(4-methoxy-benzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,3-dibromo-4-hydroxy-1-(4-methoxy-benzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (4.05 g), and NBS (1.61 g) in MeCN (30 mL) was refluxed for 10 min, then the reaction mixture was cooled with ice/water bath, the precipitates were collected as the desired product (1.418 g). The title compound, ESI MS (m/z): 583 (M+H)+.

Workup

  1. temperaturewas refluxed for 10 min
  2. temperaturethe reaction mixture was cooled with ice/water bath
  3. customthe precipitates were collected as the desired product (1.418 g)

Sources & evidence

ORD record
ord-8f0ac915c53c43a38e8b333abc1a10f8
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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