Pyridiniumtribromide → ethyl 3-bromo-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

HRID 550892

Reaction equation

HRID 550892 reaction equation
[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[Br-:15].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>N1C=CC=CC=1>[Br:15][C:3]1[C:4]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[NH:1][C:2]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 2

HCID 21124087PyridiniumtribromideHCID 21819001ethyl 1H-pyrrolo[2,3-c]pyridine-2-carboxylate

Product 1

HCID 57445353ethyl 3-bromo-1H-pyrrolo[2,3-c]pyridine-2-carboxylateYield 99.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of 2.24 g of ethyl 1H-pyrrolo[2,3-c]pyridine-2-carboxylate in 150 mL of pyridine is added dropwise a solution of 3.53 g of pyridinium tribromide in 30 mL of pyridine, at 5° C. The reaction mixture is then stirred for 16 hours at a temperature in the region of 20° C., and then washed with 500 mL of ice-cold water. The suspension is filtered. The resulting solid is washed with water and then dried in a vacuum oven at 40° C. 1.97 g of ethyl 3-bromo-1H-pyrrolo[2,3-c]pyridine-2-carboxylate are obtained, the characteristics of which are as follows:

Workup

  1. customat 5° C
  2. washwashed with 500 mL of ice-cold water
  3. filtrationThe suspension is filtered
  4. washThe resulting solid is washed with water
  5. customdried in a vacuum oven at 40° C

Sources & evidence

ORD record
ord-2b97f6f7410e4586944e27c02e51a215
Source dataset
uspto-grants-2011_05
Patent number
US07947706B2

Linked notes

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