2,2'-Bipyridine → HCID 46911039, compound

HRID 1404636Notes

Reaction equation

HRID 1404636 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:25])[CH2:9][O:10][C:11]2[CH:24]=[CH:23][C:14]([CH:15]=[C:16]3[S:20][C:19](=[O:21])[NH:18][C:17]3=[O:22])=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1C1C=CC=CN=1.[BH4-].[Na+].[BH4-]>C1COCC1.O.[Co](Cl)Cl.CC(O)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:25])[CH2:9][O:10][C:11]2[CH:24]=[CH:23][C:14]([CH2:15][CH:16]3[S:20][C:19](=[O:21])[NH:18][C:17]3=[O:22])=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 14742,2'-BipyridineHCID 28123BorohydrideHCID 4311764Sodium borohydrideHCID 86645075HCID 86645075, compound

Product 1

HCID 46911039HCID 46911039, compoundYield 72%

Reagents, catalysts & solvents 4

HCID 24288Cobalt(II) chlorideCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-{4-[2-(3-fluorophenyl)-2-hydroxyethoxy]benzylidene}-1,3-thiazolidine-2,4-dione (1.00 g, 2.78 mmol) was suspended in THF (15 mL) and H2O (10 mL). To this solution was added a small crystal of cobalt chloride followed by 2,2′-bipyridine (98 mg, 0.63 mmol). NaBH4 was added in portions until blue color persisted. The color gradually faded and was regenerated repeatedly by small additions of borohydride and HOAc. When HPLC analysis indicated that the reaction was complete, the reaction mixture was partitioned between EtOAc and H2O. HOAc was added until the pH of the aqueous phase was ca. 6. The aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was chromatographed on a small silica gel column eluting with 20% EtOAc/DCM. Fractions containing product were combined and evaporated in vacuo to give 0.72 g (72%) of the title compound as a white solid. This material was rechromatographed on a small silica column eluting with 10-20% EtOAc/DCM. MS (ESI−) for C18H16FNO4S m/z 360.1 (M−H)−.

Workup

  1. customthe reaction mixture was partitioned between EtOAc and H2O
  2. additionHOAc was added until the pH of the aqueous phase
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was chromatographed on a small silica gel column
  9. washeluting with 20% EtOAc/DCM
  10. additionFractions containing product
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-86b48960229b49059beb8d0371a3c51e
Source dataset
uspto-grants-2014_12
Patent number
US08912335B2

Reaction notes

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