Chlorosuccinimide → HCID 53412619, compound

HRID 537175Notes

Reaction equation

HRID 537175 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., 1H), 8.92 (d, J=2.0 Hz, 1H), 8.31 (d, J=1.8 Hz, 1H), 8.08 (d, J=3.1 Hz, 1H), 3.88 (s, 3H).

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-716f77d96f0241b9a2692fc200b98b65
Source dataset
uspto-grants-2014_10
Patent number
US08859773B2

Reaction notes

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