Sodium Hydroxide → 4-Chloro-1H-pyrrolo[2,3-b]pyridine

HRID 1506193Notes

Reaction equation

HRID 1506193 reaction equation
[NH:1]1[C:5]2=[N+:6]([O-])[CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.CS([Cl:15])(=O)=O.[OH-].[Na+]>CN(C)C=O.O>[Cl:15][C:9]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:1][CH:2]=[CH:3][C:4]=12

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 178526243HCID 178526243, compound

Product 1

HCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridineYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
73 °C

Procedure

1H-Pyrrolo[2,3-b]pyridine 7-oxide (4.95 g, 36.9 mmol) in N,N-dimethylformamide (10 mL) was heated to 50° C., mixed with methanesulfonyl chloride (8.00 mL, 103 mmol) and stirred at 73° C. for 3 hours. The reaction mixture was cooled with ice and diluted with water (70 mL), neutralized with sodium hydroxide and stirred for 10 minutes under cooling with ice. The precipitated solid was collected by filtration, washed with water and dried under reduced pressure to give the title compound as a reddish brown solid (4.65 g, yield 83%).

Workup

  1. temperatureThe reaction mixture was cooled with ice
  2. stirringstirred for 10 minutes
  3. temperatureunder cooling with ice
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-689c9121268a49ca8997d74443d3287c
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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