Water → 4-Chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 2240222Notes

Reaction equation

HRID 2240222 reaction equation
CS([Cl:5])(=O)=O.[CH3:6][C:7]1[C:15]2[C:10](=[N+:11]([O-])[CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1.O.[OH-].[Na+]>CN(C=O)C>[Cl:5][C:14]1[CH:13]=[CH:12][N:11]=[C:10]2[NH:9][CH:8]=[C:7]([CH3:6])[C:15]=12

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 178430808HCID 178430808, compound

Product 1

HCID 179793234-Chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
59 °C

Procedure

At 50° C., 1.77 ml (22.81 mmol) of methanesulfonyl chloride are added dropwise to a solution of 1.30 g (8.77 mmol) of 3-methyl-1H-pyrrolo[2,3-b]pyridine 7-oxide in 7.5 ml of DMF such that the temperature increases to 59° C. The mixture is then stirred at 70° C. for 4 h. After cooling to room temperature, 30 ml of water are added slowly, at 5° C., the pH is adjusted to 10 by addition of 20% strength sodium hydroxide solution and the mixture is stirred for another hour. The precipitated solid is filtered off, washed with water and then dried under reduced pressure.

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringthe mixture is stirred for another hour
  3. filtrationThe precipitated solid is filtered off
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-6cf7637c71944f71baac69c32bfaf8a2
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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