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

HRID 400383Notes

Reaction equation

HRID 400383 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.CN(C)C=O.CS([Cl:20])(=O)=O.[OH-].[Na+]>O>[Cl:20][C:9]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:1][CH:2]=[CH:3][C:4]=12

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 178526243HCID 178526243, compound

Product 1

HCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridineYield 135.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
73 °C

Procedure

To a 50° C. pink solution of 1H-pyrrolo[2,3-b]pyridine 7-oxide (2.47 g, 0.0184 mol) in N,N-dimethylformamide (13.3 mL, 0.172 mol) was added methanesulfonyl chloride (4.0 mL, 0.052 mol). The pink color changed to orange. The mixture was heated to 73° C. for 2 h, and cooled to 40° C. Then 35 mL of water was added and the resulting suspension was cooled to 0° C. NaOH was added to adjust the pH of the mixture to ˜7. The mixture was filtered and washed with water (×3) to give 3.8 g of wet pale orange solid that was dried at 40° C. overnight to give 2.35 g (82.2% yield).

Workup

  1. temperaturecooled to 40° C
  2. temperaturethe resulting suspension was cooled to 0° C
  3. filtrationThe mixture was filtered
  4. washwashed with water (×3)

Sources & evidence

ORD record
ord-e498f861ae174ada895725af89f3a418
Source dataset
uspto-grants-2014_06
Patent number
US08741895B2

Reaction notes

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