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

HRID 2070013Notes

Reaction equation

HRID 2070013 reaction equation
[N+:1]1([O-])[CH:2]=[CH:3][C:4]2[C:9]=1[NH:8][CH:7]=[CH:6][CH:5]=2.CS([Cl:15])(=O)=O.[OH-].[Na+]>CN(C=O)C>[Cl:15][C:5]1[CH:6]=[CH:7][N:8]=[C:9]2[NH:1][CH:2]=[CH:3][C:4]=12

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 178526233HCID 178526233, compound

Product 1

HCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridineYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

7-Azaindole N-oxide (43.6 g, 325 mmol) was dissolved in anhydrous DMF (280 mL), and methanesulfonyl chloride (d=1.477, 80 mL, 1.03 mol) was dropwise added thereto under an argon atmosphere. The resulting mixture was stirred at 70° C. for 90 minutes. The reaction content was poured onto ice (1 kg) and was neutralized with a 5 N sodium hydroxide solution (400 mL). The precipitated solid was collected by filtration under reduced pressure, washed with iced-water, and dried under reduced pressure using an oil pump to give 34.7 g of 4-chloro-1H-pyrrolo[2,3-b]pyridine (yield: 70%).

Workup

  1. additionThe reaction content was poured onto ice (1 kg)
  2. filtrationThe precipitated solid was collected by filtration under reduced pressure
  3. washwashed with iced-water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-61bdb516502a4ff8a98f409b855670df
Source dataset
uspto-grants-2012_10
Patent number
US08299252B2

Reaction notes

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