2,2'-Bipyridine → 5-{4-[2-Hydroxy-2-(2-methoxyphenyl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione

HRID 2274343Notes

Reaction equation

HRID 2274343 reaction equation
[OH:1][CH:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH3:26])[CH2:3][O:4][C:5]1[CH:18]=[CH:17][C:8](/[CH:9]=[C:10]2/[C:11](=[O:16])[NH:12][C:13](=[O:15])[S:14]/2)=[CH:7][CH:6]=1.N1C=CC=CC=1C1C=CC=CN=1.[BH4-].[Na+].[BH4-]>C1COCC1.[Co](Cl)Cl.CC(O)=O.O>[OH:1][CH:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH3:26])[CH2:3][O:4][C:5]1[CH:18]=[CH:17][C:8]([CH2:9][CH:10]2[S:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])=[CH:7][CH:6]=1

Participants

9

Reactant 4

HCID 14742,2'-BipyridineHCID 28123BorohydrideHCID 4311764Sodium borohydrideHCID 86645078(5Z)-5-{4-[2-hydroxy-2-(2-methoxyphenyl)ethoxy]benzylidene}-1,3-thiazolidine-2,4-dione

Product 1

HCID 469110385-{4-[2-Hydroxy-2-(2-methoxyphenyl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dioneYield 63%

Reagents, catalysts & solvents 4

HCID 24288Cobalt(II) chlorideCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

(5Z)-5-{4-[2-hydroxy-2-(2-methoxyphenyl)ethoxy]benzylidene}-1,3-thiazolidine-2,4-dione (1.00 g, 2.69 mmol) was dissolved in THF (20 mL). Water (20 mL) was added and then sufficient additional THF was added to give a clear solution. A small crystal of cobalt chloride was added followed by 2,2′-bipyridine (95 mg, 0.61 mmol). The reaction mixture was cooled to 0° C. NaBH4 was added in portions until the blue color persisted. The color gradually faded and was regenerated repeatedly by small additions of borohydride and HOAc. When HPLC 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, and 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 0.63 g (63%) of the title compound as a white solid. MS (ESI−) for C19H19NO5S m/z 372.1 (M−H)−.

Workup

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

Sources & evidence

ORD record
ord-f9b9d79610f640708f5fbeb06c1f0619
Source dataset
uspto-grants-2015_09
Patent number
US09126959B2

Reaction notes

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