Chlorosuccinimide → 3-Chloro-1,2-bis-(4-fluoro-phenyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642229Notes

Reaction equation

HRID 642229 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:29])=[C:8]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[N:12]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].[Cl:30]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl.C(OOC(C1C=CC=CC=1)=O)(C1C=CC=CC=1)=O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:29])=[C:8]2[C:14]([Cl:30])=[C:13]([C:15]3[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=3)[N:12]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 684282431,2-Bis-(4-fluoro-phenyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 684277533-Chloro-1,2-bis-(4-fluoro-phenyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl esterYield 74.7%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

The mixture of 1,2-bis-(4-fluoro-phenyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (80 mg, 0.203 mmol), N-chlorosuccinimide (NCS)(28 mg, 0.203 mmol) and BzOOBz (2.5 mg) in tetrachloromethane (6 mL) was refluxed overnight, then the solvents were removed, the residue was purified on column to give the desired title compound (65 mg); ESI MS (m/z): 429 (M+H+).

Workup

  1. temperaturewas refluxed overnight
  2. customthe solvents were removed
  3. customthe residue was purified on column

Sources & evidence

ORD record
ord-2914284086df49c4a6cb581ab2f94ef0
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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