Chlorosuccinimide → HCID 53412619, compound

HRID 2403685Notes

Reaction equation

HRID 2403685 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.[Cl:14]N1C(=O)CCC1=O>CN(C)C=O.O>[Cl:14][C:3]1[C:4]2=[N:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=[C:9]2[NH:1][CH:2]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 11672756Methyl 1H-pyrrolo[3,2-b]pyridine-6-carboxylate

Product 1

HCID 53412619HCID 53412619, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a 0° C. solution of methyl 1H-pyrrolo[3,2-b]pyridine-6-carboxylate (1.00 g, 5.68 mmol) in N,N-dimethylformamide (15 mL) was added N-chlorosuccinimide (895 mg, 5.96 mmol). The reaction was allowed to gradually warm to room temperature and stir overnight. The reaction was diluted with water (125 mL) and stirred for 20 minutes. The resulting solid was collected by filtration, washed with water, and dried under vacuum to give the title compound (1.11 g, 93%) as an orange powder. +ESI (M+H) 211.0; 1H NMR (400 MHz, DMSO-d6, δ): 11.99 (br. s., 1 H), 8.92 (d, J=2.0 Hz, 1 H), 8.31 (d, J=1.8 Hz, 1 H), 8.08 (d, J=3.1 Hz, 1 H), 3.88 (s, 3 H).

Workup

  1. stirringstirred for 20 minutes
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-29ff3a22e60540b6b98d71dc2479d9a6
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

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