Chlorosuccinimide → 3-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid

HRID 537187Notes

Reaction equation

HRID 537187 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([C:10]([OH:12])=[O:11])[CH:9]=[C:4]2[CH:3]=[CH:2]1.[Cl:13]N1C(=O)CCC1=O>CN(C)C=O.O>[Cl:13][C:3]1[C:4]2[C:5](=[N:6][CH:7]=[C:8]([C:10]([OH:12])=[O:11])[CH:9]=2)[NH:1][CH:2]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 219070181H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid

Product 1

HCID 674914623-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acidYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A suspension of 1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (250 mg, 1.5 mmol) in N,N-dimethylformamide (5 mL) was warmed to 40° C. N-chlorosuccinimide (243 mg, 1.62 mmol) was added and the mixture was stirred at 55° C. for 5 hours. The reaction was cooled to room temperature and left stirring for 2 days. The mixture was diluted with water (20 mL) and stirred overnight. The resulting solid was collected by filtration and dried to give the title compound (161 mg, 55%). +ESI (M+H) 197.1; 1H NMR (400 MHz, DMSO-d6, δ): 13.08 (br. s., 1H), 12.39 (br. s., 1H), 8.86 (d, J=1.8 Hz, 1H), 8.40 (d, J=1.2 Hz, 1H), 7.84 (d, J=2.5 Hz, 1H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. waitleft
  3. stirringstirring for 2 days
  4. stirringstirred overnight
  5. filtrationThe resulting solid was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-a9135dea712d4cf283735c3014ff736c
Source dataset
uspto-grants-2014_10
Patent number
US08859773B2

Reaction notes

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