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p-Bromochlorobenzene → 1-(4-Chlorophenyl)-1H-pyrrolo[2,3-c]pyridine

HRID 588403
Notes
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Reaction equation

HRID 588403 reaction equation
[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.Br[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([N:1]2[C:5]3=[CH:6][N:7]=[CH:8][CH:9]=[C:4]3[CH:3]=[CH:2]2)=[CH:12][CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7806p-BromochlorobenzeneHCID 92196-AzaindoleHCID 62657Potassium Phosphate, Tribasic

Product 1

HCID 574026561-(4-Chlorophenyl)-1H-pyrrolo[2,3-c]pyridineYield 91%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst
HCID 31275
1,4-Dioxane
Solvent

Procedure

A suspension of 1H-pyrrolo[2,3-c]pyridine (1.18 g, 10.0 mmol), 1-bromo-4-chlorobenzene (2.87 g, 15.0 mmol), copper(I) iodide (95.0 mg, 0.50 mmol), K3PO4 (4.46 g, 21.0 mmol) and trans-diaminocyclohexane (250 μL, 2.00 mmol) in 1,4-dioxane (15 mL) was heated to reflux for 5 days. The mixture was concentrated and the residue was purified by flash chromatography (EtOAc) to yield the title compound as a light brown solid (2.08 g, 90%). MS (ESI+) m/z=229, 231 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 days
  3. concentrationThe mixture was concentrated
  4. customthe residue was purified by flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-a1701057894346bbb1d550125b27b1fb
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09227967B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes