2,2'-Bipyridine → HCID 68109280, compound

HRID 385076Notes

Reaction equation

HRID 385076 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:19]=[C:20](I)[C:21]=1[OH:22])[C:6]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10](=[O:18])(=[O:17])[CH2:9]1)=[O:7])#[N:2].N1C=CC=C[C:25]=1C1C=CC=CN=1.[CH3:36][S:37]SC>CN(C)C=O.[Zn].[Ni](Br)Br>[C:1]([C:3]1[CH:4]=[C:5]([CH:19]=[C:20]([S:37][CH3:36])[C:21]=1[O:22][CH3:25])[C:6]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10](=[O:18])(=[O:17])[CH2:9]1)=[O:7])#[N:2]

Participants

7

Reactant 3

HCID 14742,2'-BipyridineHCID 12232Dimethyl DisulfideHCID 68108727HCID 68108727, compound

Product 1

HCID 68109280HCID 68109280, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 278492Nickel(II) bromideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

3-(3-cyano-4-hydroxy-5-iodobenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole (334 mg) was dissolved in N,N-dimethylformamide (3.5 mL), and 2,2′-bipyridine (11 mg), zinc powder (95 mg), nickel bromide (16 mg) and dimethyl disulfide (0.04 mL) were added to the solution, and then the mixture was stirred at 80° C. for 1 hour. 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 (3 mL). Potassium carbonate (298 mg) and dimethylsulfuric acid (0.13 mL) was added to the solution, and then the mixture was stirred at room temperature for 1 hour. Water was added to the reaction solution, and then the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and 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=2:1) to obtain the title compound (142 mg) as a pale yellow oily substance.

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 (3 mL)
  8. additionPotassium carbonate (298 mg) and dimethylsulfuric acid (0.13 mL) was added to the solution
  9. stirringthe mixture was stirred at room temperature for 1 hour
  10. additionWater was added to the reaction solution
  11. extractionthe reaction mixture was extracted with ethyl acetate
  12. washThe organic layer was washed with water and 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=2:1)

Sources & evidence

ORD record
ord-b39dce9256b841ffa2880bf3daaec670
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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