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

HRID 642270
Notes
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Reaction equation

HRID 642270 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:21])=[C:8]2C=[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:48]([Cl:52])(Cl)(Cl)Cl>>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:21])=[C:8]2[C:48]([Cl:52])=[CH:13][N:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]2=[C:10]([Cl:29])[N:11]=1)=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 5943Carbon TetrachlorideHCID 7187Benzoyl PeroxideHCID 31398ChlorosuccinimideHCID 684267014-Hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 866173533,7-Dichloro-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Procedure

A mixture of 4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (270 mg, 0.956 mmol), NCS (269 mg, 2.01 mmol) and BzOOBz (12 mg, 0.048 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 (173 mg). The title compound, 1H NMR (200 MHz, CDCl3): δ (ppm)=11.8 (s, 1H), 7.6-7.3 (m, 6H), 4.52 (q, 2H, J=6.8 Hz), 1.47 (t, 3H, J=6.8 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-3233b4c034124873ac3561dd5d1e9322
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07696223B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes