2,2'-Bipyridine → HCID 57786250, compound

HRID 1399037Notes

Reaction equation

HRID 1399037 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[NH:11][CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1I.N1C=CC=CC=1C1C=CC=CN=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C.[Cu]I>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:22]4[CH:21]=[CH:20][C:19]([Cl:18])=[CH:24][C:23]=4[Cl:25])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 14742,2'-BipyridineHCID 10796Cesium carbonateHCID 968642,4-Dichloro-1-iodobenzeneHCID 1363879919-Chloro-6-nitro-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole

Product 1

HCID 57786250HCID 57786250, compoundYield 5%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 9-chloro-6-nitro-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole (Reference Example 108; 10.0 g, 39.6 mmol), 2,4-dichloro-1-iodobenzene (54.0 g, 197.9 mmol), copper(I) iodide (7.57 g, 39.6 mmol), 2,2′-bipyridyl (12.3 g, 79.2 mmol) and cesium carbonate (25.8 g, 79.2 mmol) in N,N-dimethylformamide (600 mL) was stirred at 150° C. for 12 hr. The mixture was diluted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 10-25% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound (750 mg, 1.88 mmol, 5%) as a light yellow amorphous.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography on silica gel eluting with a 10-25% ethyl acetate/n-hexane gradient mixture
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e26b6984be9b48dca6b8afe07e07f234
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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