Sodium Carbonate → HCID 69545801, compound

HRID 1744685Notes

Reaction equation

HRID 1744685 reaction equation
FC(F)(F)S(O[C:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][C:8]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21])(=O)=O.[F:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:27][C:28]1[CH:33]=[CH:32][C:31]([C:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:9][C:8]=2[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:30][CH:29]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 222284091-(tert-Butyl) 3-ethyl 4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1,3(2H)-dicarboxylate

Product 1

HCID 69545801HCID 69545801, compoundYield 87.9%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolventHCID 21863594Toluene ethanolSolvent

Conditions

Temperature
80 °C

Procedure

A vigorously stirred suspension of the product of step C (1.00 g, 2.48 mmol), 4-fluorophenylboronic acid (0.382 g, 2.73 mmol) and [1,1′-bis(diphenylphosphino)-ferrocene)dichloropalladium(II) (0.102 g, 0.124 mmol) in toluene/ethanol (3:2; 24.0 mL) was degassed via three vacuum/nitrogen ingress cycles and then heated to approximately 80° C. Aqueous 2 M sodium carbonate (3.10 mL, 6.20 mmol) was added dropwise via syringe and the resulting mixture maintained at reflux overnight. After cooling to ambient temperature, the reaction mixture was diluted with ethyl acetate and filtered through celite®. The filtrate was poured into water and extracted three times with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification of the residue by medium pressure liquid chromatography on silica gel (gradient elution; 0–15% ethyl acetate/hexanes as eluent) afforded the title compound as a colorless oil (0.762 g).

Workup

  1. customwas degassed via three vacuum/nitrogen ingress cycles
  2. temperaturethe resulting mixture maintained
  3. temperatureat reflux overnight
  4. temperatureAfter cooling to ambient temperature
  5. filtrationfiltered through celite®
  6. additionThe filtrate was poured into water
  7. extractionextracted three times with ethyl acetate
  8. washThe combined organic extracts were washed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo
  11. customPurification of the residue by medium pressure liquid chromatography on silica gel (gradient elution; 0–15% ethyl acetate/hexanes as eluent)

Sources & evidence

ORD record
ord-a55ccc77b2344db498f31461fd5a3774
Source dataset
uspto-grants-2006_03
Patent number
US07015235B2

Reaction notes

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