1,10-Phenanthroline → 3-{3-[3-(1,3-thiazol-2-yl)-1H-pyrrol-1-yl]phenyl}pyridine

HRID 746828Notes

Reaction equation

HRID 746828 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[S:7][CH:8]=[CH:9][N:10]=2)=[CH:2]1.N1C2[C:15](=[CH:16][CH:17]=[C:18]3[C:23]=2[N:22]=[CH:21][CH:20]=[CH:19]3)[CH:14]=[CH:13][CH:12]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I>[S:7]1[CH:8]=[CH:9][N:10]=[C:6]1[C:3]1[CH:4]=[CH:5][N:1]([C:15]2[CH:16]=[C:17]([C:18]3[CH:23]=[N:22][CH:21]=[CH:20][CH:19]=3)[CH:12]=[CH:13][CH:14]=2)[CH:2]=1

Participants

6

Reactant 3

HCID 13181,10-PhenanthrolineHCID 62657Potassium Phosphate, TribasicHCID 1362498942-(1H-Pyrrol-3-yl)-1,3-thiazole

Product 1

HCID 113241343-{3-[3-(1,3-thiazol-2-yl)-1H-pyrrol-1-yl]phenyl}pyridine

Reagents, catalysts & solvents 2

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

Procedure

A solution of 2-(1H-pyrrol-3-yl)-1,3-thiazole (0.100 g, 0.67 mmol) 3-(3-iodophenyl)pyridine (0.224 g, 0.8 mmol), copper(I) iodide (0.038 g, 0.2 mmol), 1,10-phenanthroline (0.360 g, 2 mmol), potassium phosphate (0.440 g, 2.0 mmol) in dioxane (2 mL) was heated at 220° C. for ½ hr under microwave irradiation. 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 (EtOAc 100%) to afford 3-{3-[3-(1,3-thiazol-2-yl)-1H-pyrrol-1-yl]phenyl}pyridine as a slightly yellow oil. The free base in anhydrous diethyl ether was treated with 1.5 equivalent HCl (1M in Ether) to give 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 (EtOAc 100%)

Sources & evidence

ORD record
ord-d2c3ee5e296d4d22849b91fa452915cd
Source dataset
uspto-grants-2008_07
Patent number
US07393959B2

Reaction notes

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