Benzoyl Peroxide → 3-Chloro-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642269Notes

Reaction equation

HRID 642269 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:21])=[C:8]2[CH:14]=[CH:13][N:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].C1C(=O)N([Cl:29])C(=O)C1.C(OOC(C1C=CC=CC=1)=O)(C1C=CC=CC=1)=O>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:21])=[C:8]2[C:14]([Cl:29])=[CH:13][N:12]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 31398ChlorosuccinimideHCID 684267014-Hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 684287393-Chloro-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl esterYield 40%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (223 mg, 0.789 mmol), NCS (117 mg, 0.869 mmol) and BzOOBz (10 mg, 0.039 mmol) in carbontetrachloride (4 mL) was refluxed for 30 min. Then the reaction was cooled and concentrated, the resulting mixture was purified by column to give the desired product (100 mg). The title compound, 1H NMR (200 MHz, CDCl3): δ (ppm)=11.8 (s, 1H), 8.44 (s, 1H), 7.6-7.4 (m, 5H), 7.35 (s, 1H), 4.53 (q, 2H, J=7.4 Hz), 1.49 (t, 3H, J=7.4 Hz).

Workup

  1. temperaturewas refluxed for 30 min
  2. temperatureThen the reaction was cooled
  3. concentrationconcentrated
  4. customthe resulting mixture was purified by column

Sources & evidence

ORD record
ord-97505596a6de45589efffadac3d22563
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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