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

HRID 642266Notes

Reaction equation

HRID 642266 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(OOC(C1C=CC=CC=1)=O)(C1C=CC=CC=1)=O.[C:49]([Cl:53])(Cl)(Cl)Cl>>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:22])=[C:8]2[C:49]([Cl:53])=[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 4

HCID 5943Carbon TetrachlorideHCID 7187Benzoyl PeroxideHCID 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

Procedure

A mixture of 1-benzyl-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (1.814 g, 6.12 mmol), NCS (1.72 g, 12.85 mmol) and BzOOBz (75 mg, 0.31 mmol) in carbontetrachloride (30 mL) was refluxed for 60 min. Then the reaction was cooled and concentrated, the resulting mixture was purified by column to give the title compound (1.469 mg) ESI MS (m/z) 365 (M+H)+; and a by-product, 1-benzyl-2,3,7-trichloro-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester as by product (90 mg) ESI MS (m/z): 399 (M+H)+.

Workup

  1. temperaturewas refluxed for 60 min
  2. temperatureThen the reaction was cooled
  3. concentrationconcentrated
  4. customthe resulting mixture was purified by column

Sources & evidence

ORD record
ord-883e91bba75544719dd02f4a2ac60973
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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