2,2'-Bipyridine → HCID 68108455, compound

HRID 385094Notes

Reaction equation

HRID 385094 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19](I)[C:20]=1[OH:21])[C:5]([N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:9](=[O:17])(=[O:16])[CH2:8]1)=[O:6].N1C=CC=C[C:24]=1C1C=CC=CN=1.[CH3:35][S:36]SC>CN(C)C=O.[Zn].[Ni](Br)Br>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([S:36][CH3:35])[C:20]=1[O:21][CH3:24])[C:5]([N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:9](=[O:17])(=[O:16])[CH2:8]1)=[O:6]

Participants

7

Reactant 3

HCID 14742,2'-BipyridineHCID 12232Dimethyl DisulfideHCID 68109178HCID 68109178, compound

Product 1

HCID 68108455HCID 68108455, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 278492Nickel(II) bromideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

3-(3-chloro-4-hydroxy-5-iodobenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole (1.19 g) was dissolved in N,N-dimethylformamide (9 mL), and 2,2′-bipyridine (32 mg), a zinc powder (262 mg), nickel bromide (45 mg) and dimethyl disulfide (0.09 mL) were added to the solution, and then the mixture was stirred at 80° C. for 1.5 hours. After the reaction solution was filtered, 1N hydrochloric acid was added and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was dissolved in N,N-dimethylformamide (6 mL). Potassium carbonate (828 mg) and dimethylsulfuric acid (0.38 mL) was added to the solution, and then the mixture was stirred at room temperature for 14 hours. Water was added to the reaction solution, and then the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to obtain the title compound (203 mg) as a yellow crystal.

Workup

  1. filtrationAfter the reaction solution was filtered
  2. addition1N hydrochloric acid was added
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. dissolutionthe obtained residue was dissolved in N,N-dimethylformamide (6 mL)
  8. additionPotassium carbonate (828 mg) and dimethylsulfuric acid (0.38 mL) was added to the solution
  9. stirringthe mixture was stirred at room temperature for 14 hours
  10. additionWater was added to the reaction solution
  11. extractionthe reaction mixture was extracted with ethyl acetate
  12. washThe organic layer was washed with saturated brine
  13. dry with materialdried over anhydrous sodium sulfate
  14. distillationThe solvent was distilled off under reduced pressure
  15. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-df3bd6aa7ad34fb0b6161d87c6b0094d
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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