2,2'-Bipyridine → HCID 51349325, compound

HRID 385138Notes

Reaction equation

HRID 385138 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=CC=1C1C=CC=CN=1.[CH2:36]([S:38]SCC)[CH3:37]>CN(C)C=O.[Zn].[Ni](Br)Br>[C:1]([C:3]1[CH:4]=[C:5]([CH:19]=[C:20]([S:38][CH2:36][CH3:37])[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]

Participants

7

Reactant 3

HCID 14742,2'-BipyridineHCID 8077Diethyl disulfideHCID 68108727HCID 68108727, compound

Product 1

HCID 51349325HCID 51349325, compoundYield 29.4%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 278492Nickel(II) bromideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

3-(3-cyano-4-hydroxy-5-iodobenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole (500 mg) was dissolved in N,N-dimethylformamide (5 mL), and 2,2′-bipyridine (18 mg), zinc powder (149 mg), nickel bromide (25 mg) and diethyl disulfide (70 mg) were added to the solution, and then the mixture was stirred at 110° 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 purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) and then crystallized from diethylether-ethyl acetate to obtain the title compound (63 mg) as a colorless 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. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)
  8. customcrystallized from diethylether-ethyl acetate

Sources & evidence

ORD record
ord-2a0be1146f9c400ca522a3e035dccf13
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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