Carbon Tetrachloride → 1-Benzyl-3,7-dichloro-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642258Notes

Reaction equation

HRID 642258 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:22])=[C:8]2C=[CH:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].C1C(=O)N([Cl:30])C(=O)C1.[C:31]([Cl:35])(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:22])=[C:8]2[C:31]([Cl:35])=[CH:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]2=[C:10]([Cl:30])[N:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 31398ChlorosuccinimideHCID 684277721-Benzyl-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 866173511-Benzyl-3,7-dichloro-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 7187Benzoyl PeroxideCatalyst

Procedure

A mixture of 1-benzyl-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (60 mg, 0.202 mmol), NCS (57 mg, 0.424 mmol), and BzOOBz (2.4 mg, 0.01 mmol) in carbontetrachloride was refluxed for 1 hour. Then the reaction was cooled, solvent was removed, and the resulting residue was purified on column to give the title compound (48 mg). The title compound: ESI MS (m/z): 410 (M+H+).

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperatureThen the reaction was cooled
  3. customsolvent was removed
  4. customthe resulting residue was purified on column

Sources & evidence

ORD record
ord-1c47cf2db7ef406db2628c2b3ba7886b
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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