2,2'-Bipyridine → HCID 46911090, compound

HRID 562937Notes

Reaction equation

HRID 562937 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([OH:25])[CH2:9][O:10][C:11]1[CH:24]=[CH:23][C:14]([CH:15]=[C:16]2[S:20][C:19](=[O:21])[NH:18][C:17]2=[O:22])=[CH:13][CH:12]=1.[OH-].[Na+].N1C=CC=CC=1C1C=CC=CN=1.[BH4-].[Na+]>C1COCC1.O.O.O.O.O.O.O.[Co](Cl)Cl.CC(O)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([OH:25])[CH2:9][O:10][C:11]1[CH:24]=[CH:23][C:14]([CH2:15][CH:16]2[S:20][C:19](=[O:21])[NH:18][C:17]2=[O:22])=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 14742,2'-BipyridineHCID 14798Sodium HydroxideHCID 4311764Sodium borohydride3×HCID 86645073HCID 86645073, compound

Product 1

HCID 46911090HCID 46911090, compoundYield 63.2%

Reagents, catalysts & solvents 3

HCID 517166Dichlorocobalt hexahydrateCatalystHCID 176Acetic AcidSolvent3×HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a stirring mixture of 5-{4-[2-(2-fluorophenyl)-2-hydroxyethoxy]benzylidene}-1,3-thiazolidine-2,4-dione (0.52 g, 1.40 mmol) in THF/H2O (1:1, 16 ml) was added 1M NaOH (2 ml), cobalt (II) chloride hexahydrate (0.2 mg, 0.0009 mmol), 2,2′-bipyridine (50.8 mg, 0.33 mmol), and finally sodium tetrahydroborate (0.11 g, 2.90 mmol). The reaction turned a deep blue/purple color. After a short time, the dark color began to fade and HOAc was added dropwise to regenerate the darker color. When the color faded and addition of HOAc failed to regenerate it, NaBH4 was added to regenerate the darker color. Added small portions of NaBH4 and HOAc dropwise until deep blue color persisted. After repeating this several times, HPLC indicated that the reaction was complete despite the fact that the deep blue color has given way to a light brown solution. The reaction was partitioned between water and EtOAc. The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The resulting light brown oil was chromatographed, eluting with 35% EtOAc/hexanes. Fractions containing compound were combined and evaporated in vacuo to give 0.32 g of the title compound as a white solid. MS (ESI−) for C18H16FNO4S m/z 360.1 (M−H)−.

Workup

  1. additionwas added
  2. customThe reaction was partitioned between water and EtOAc
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe resulting light brown oil was chromatographed
  8. washeluting with 35% EtOAc/hexanes
  9. additionFractions containing compound
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-f885c1938bfc484683f81e3aba9887dc
Source dataset
uspto-grants-2011_11
Patent number
US08067450B2

Reaction notes

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