2,2'-Bipyridine → 8-Chloro-5-(1-ethylpropyl)-1-(3-methyl-5-nitropyridin-2-yl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole

HRID 1399139Notes

Reaction equation

HRID 1399139 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[NH:11][CH2:12][CH2:13][N:7]3[C:6]=2[C:5]([CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[CH:4][CH:3]=1.Br[C:20]1[C:25]([CH3:26])=[CH:24][C:23]([N+:27]([O-:29])=[O:28])=[CH:22][N:21]=1.N1C=CC=CC=1C1C=CC=CN=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1CCCC1=O.C(OCC)(=O)C.[Cu]I>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:20]4[C:25]([CH3:26])=[CH:24][C:23]([N+:27]([O-:29])=[O:28])=[CH:22][N:21]=4)[CH2:12][CH2:13][N:7]3[C:6]=2[C:5]([CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 14742,2'-BipyridineHCID 10796Cesium carbonateHCID 52004662-Bromo-3-methyl-5-nitropyridineHCID 1360477328-Chloro-5-(1-ethylpropyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole

Product 1

HCID 577863098-Chloro-5-(1-ethylpropyl)-1-(3-methyl-5-nitropyridin-2-yl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 8-chloro-5-(1-ethylpropyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole (30.6 mg, 0.116 mmol), 2-bromo-3-methyl-5-nitropyridine (50.4 mg, 0.232 mmol), copper(I) iodide (22.1 mg, 0.116 mmol), 2,2′-bipyridyl (36.2 mg, 0.232 mmol) and cesium carbonate (75.6 mg, 0.232 mmol) in 1-methyl-2-pyrrolidinone (1.0 mL) was stirred at 150° C. for 5 hrs. After cooling, the mixture was diluted with ethyl acetate, the precipitate was filtered through a pad of celite. The filtrate was extracted with ethyl acetate (×3). The combined organic layer was washed with 1N hydrochloric acid (×1) and brine (×1), dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 0-30% ethyl acetate/n-hexane gradient mixture to give the title compound as a yellow amorphous (13.5 mg, 0.0338 mmol, 29%).

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was filtered through a pad of celite
  3. extractionThe filtrate was extracted with ethyl acetate (×3)
  4. washThe combined organic layer was washed with 1N hydrochloric acid (×1) and brine (×1)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with a 0-30% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-4c4d80ef6104452db343f2148170a92d
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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