2,2'-Bipyridine → HCID 57786103, compound

HRID 1628680Notes

Reaction equation

HRID 1628680 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[NH:11][CH2:12][CH2:13][CH2:14][CH2:15][N:7]3[C:6]=2[C:5]([N+:16]([O-:18])=[O:17])=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=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:23]4[CH:22]=[CH:21][C:20]([Cl:19])=[CH:25][C:24]=4[Cl:26])[CH2:12][CH2:13][CH2:14][CH2:15][N:7]3[C:6]=2[C:5]([N+:16]([O-:18])=[O:17])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 14742,2'-BipyridineHCID 10796Cesium carbonateHCID 968642,4-Dichloro-1-iodobenzeneHCID 13638799010-Chloro-7-nitro-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazole

Product 1

HCID 57786103HCID 57786103, compoundYield 45%

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 10-chloro-7-nitro-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazole (Reference Example 106; 1.74 g, 6.50 mmol), 2,4-dichloro-1-iodobenzene (8.87 g, 32.5 mmol), copper(I) iodide (1.24 g, 6.50 mmol), 2,2′-bipyridyl (2.02 g, 13.0 mmol) and cesium carbonate (4.24 g, 13.0 mmol) in N,N-dimethylformamide (100 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 (1.20 g, 2.91 mmol, 45%) 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-ced5b3e419af410581dd92afffe82b8d
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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