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1,10-Phenanthroline → HCID 9904298, compound

HRID 746822
Notes
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Reaction equation

HRID 746822 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)=[CH:2]1.I[C:13]1[CH:14]=[C:15]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:16]=[CH:17][CH:18]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I>[N:21]1[CH:22]=[CH:23][CH:24]=[C:19]([C:15]2[CH:16]=[C:17]([N:1]3[CH:5]=[CH:4][C:3]([C:6]4[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=4)=[CH:2]3)[CH:18]=[CH:13][CH:14]=2)[CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 62657Potassium Phosphate, TribasicHCID 8203972-(1H-pyrrol-3-yl)pyridineHCID 69303602HCID 69303602, compound

Product 1

HCID 9904298HCID 9904298, compound

Reagents, catalysts & solvents 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 2-(1H-pyrrol-3-yl)pyridine (0.144 g, 1.0 mmol), 3-(3-iodophenyl)pyridine (0.281 g, 1.2 mmol), 1,10-phenanthroline (0.360 g, 2 mmol), Potassium phosphate (0.445 g, 2.1 mmol), in dioxane (3 mL) was degassed with argon for 5 minutes, followed by the addition of copper (I) iodide (0.038 g, 0.2 mmol). The reaction mixture was heated at 110° C. for 4 hr. The reaction mixture was quenched with H2O (30 mL), then extracted with EtOAc (3×30 mL) and the combined organic extracts washed with brine. The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude purified by liquid chromatography on silica gel using an ISCO single channel system (Hexane/EtOAc=9/1 to 1/9) to afford 2-[1-(3-pyridin-3-ylphenyl)-1H-pyrrol-3-yl]pyridine as a slightly yellow oil. The free base in anhydrous diethyl ether was treated with 1.5 equivalents HCl (1M in ether) to give the HCl salt.

Workup

  1. customThe reaction mixture was quenched with H2O (30 mL)
  2. extractionextracted with EtOAc (3×30 mL)
  3. washthe combined organic extracts washed with brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude purified by liquid chromatography on silica gel using an ISCO single channel system (Hexane/EtOAc=9/1 to 1/9)

Sources & evidence

ORD record
ord-fe335ee6e0654b1180dfcf4b9c764b28
Source dataset
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07393959B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes