Sodium Hydroxide → 6-Bromo-4-chloro-1H-pyrrolo[2,3-B]pyridine

HRID 1878612Notes

Reaction equation

HRID 1878612 reaction equation
[Br:1][C:2]1[N:7]=[C:6]2[N:8](C(C3C=CC=CC=3)=O)[CH:9]=[CH:10][C:5]2=[C:4]([Cl:19])[CH:3]=1.[OH-].[Na+]>CO>[Br:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[C:4]([Cl:19])[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 73014178(6-Bromo-4-chloro-pyrrolo[2,3-b]pyridin-1-yl)-phenyl-methanone

Product 1

HCID 247295876-Bromo-4-chloro-1H-pyrrolo[2,3-B]pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(6-Bromo-4-chloro-pyrrolo[2,3-b]pyridin-1-yl)-phenyl-methanone (1 eq, 69.7 mmol, 23.4 g) is dissolved in MeOH (300 ml), then aqueous NaOH solution (1 M, 120 ml) is added and the resulting mixture is stirred for 18 h at r.t. The mixture is extracted with DCM and EtOAc, the extracts are combined and the solvents are removed in vacuo. Recrystallization from MeOH yields the title compound; [M+H]+=231.

Workup

  1. extractionThe mixture is extracted with DCM and EtOAc
  2. customthe solvents are removed in vacuo
  3. customRecrystallization from MeOH

Sources & evidence

ORD record
ord-34d7a9f803954f57bee3507ac7c79743
Source dataset
uspto-grants-2012_11
Patent number
US08314112B2

Reaction notes

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