Sodium Carbonate → 4-fluoro-2-methoxy-N-[2-[2-[[3-(trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]benzamide

HRID 888265

Reaktionsgleichung

Reaktionsgleichung von HRID 888265
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:11][CH3:12])[CH:3]=1.[F:13][C:14]([F:35])([F:34])[C:15]1[CH:16]=[C:17]([S:21]([CH2:24][CH2:25][S:26][C:27]2[C:32]([NH2:33])=[CH:31][CH:30]=[CH:29][N:28]=2)(=[O:23])=[O:22])[CH:18]=[CH:19][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+]>S(Cl)(Cl)=O.O1CCOCC1>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:33][C:32]2[C:27]([S:26][CH2:25][CH2:24][S:21]([C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([C:14]([F:34])([F:35])[F:13])[CH:16]=3)(=[O:23])=[O:22])=[N:28][CH:29]=[CH:30][CH:31]=2)=[O:8])=[C:4]([O:11][CH3:12])[CH:3]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 27745454-Fluoro-2-methoxybenzoic acidHCID 67133713[2-[2-[[3-(Trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]amine

Produkt 1

HCID 469178204-fluoro-2-methoxy-N-[2-[2-[[3-(trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]benzamideAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24386Thionyl ChlorideLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 510 mg (3.0 mmol) 4-fluoro-2-methoxybenzoic acid in thionyl chloride (3 ml) was stirred for 2 h at RT. Then the mixture was concentrated to small volume under vacuum and the residue was taken up with dioxane (15 ml). Then a solution of 1.09 g (3.0 mmol) [2-[2-[[3-(trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]amine (VPF-001) in dioxane (15 ml) and 1.06 g (10.0 mmol) Na2CO3 were added and the mixture was stirred for 16 h at RT. Then the mixture was concentrated to small volume under vacuum and the residue was taken up with water and extracted with EE. The organic phase was washed with a saturated aqueous NaHCO3 solution and brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Crystallisation (DCM/hexane) of the residue yielded 895 mg (1.7 mmol, 58%) 4-fluoro-2-methoxy-N-[2-[2-[[3-(trifluoromethyl)-phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]-benzamide. MS: m/z 514.1 [M+H]+.

Aufarbeitung

  1. concentrationThen the mixture was concentrated to small volume under vacuum
  2. concentrationThen the mixture was concentrated to small volume under vacuum
  3. extractionextracted with EE
  4. washThe organic phase was washed with a saturated aqueous NaHCO3 solution and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to small volume under vacuum
  8. customCrystallisation (DCM/hexane) of the residue

Quellen und Nachweise

ORD-Eintrag
ord-09b79a31a3b14fc8815f51bfdb85fac3
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247573B2

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