Ammonium Chloride → 4-Azido-5-bromo-1H-pyrrolo[2,3-b]pyridine

HRID 1693700Notes

Reaction equation

HRID 1693700 reaction equation
[Br:1][C:2]1[C:3](Cl)=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[N-:12]=[N+:13]=[N-:14].[Na+].[Cl-].[NH4+]>CN(C)C=O.O>[N:12]([C:3]1[C:2]([Br:1])=[CH:7][N:6]=[C:5]2[NH:8][CH:9]=[CH:10][C:4]=12)=[N+:13]=[N-:14]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 457897885-Bromo-4-chloro-1H-pyrrolo(2,3-b)pyridine

Product 1

HCID 575376574-Azido-5-bromo-1H-pyrrolo[2,3-b]pyridineYield 43.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

5-Bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine (1.5 g, 6.5 mmol), sodium azide (2.11 g, 32 mmol), and ammonium chloride (1.73 g, 32 mmol) were suspended in anhydrous dimethylformamide (10 mL). The reaction was heated to 110° C. for 19 h. The reaction mixture was diluted with water and the solids were collected. The solids were dissolved in a mixture of acetone and ethylacetate, the solution was filtered and concentrated to afford 4-Azido-5-bromo-1H-pyrrolo[2,3-b]pyridine (670 mg, 2.8 mmol, 43%). MS: m/z 238.0/240.0 (M+H+).

Workup

  1. customthe solids were collected
  2. dissolutionThe solids were dissolved in a mixture of acetone and ethylacetate
  3. filtrationthe solution was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-14b04ee981084b10aae1b31999ea4caf
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

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