2,2,2-Trifluoroethanesulfonyl chloride → 2,2,2-trifluoro-ethanesulfonic acid (6-{(E)-2-[3-tert-butyl-5-(5-fluoro-2-methoxy-pyridin-3-yl)-2-methoxy-phenyl]-vinyl}-pyridin-3-yl)-amide

HRID 2390867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2390867
[C:1]([C:5]1[C:6]([O:29][CH3:30])=[C:7](/[CH:20]=[CH:21]/[C:22]2[N:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=2)[CH:8]=[C:9]([C:11]2[C:12]([O:18][CH3:19])=[N:13][CH:14]=[C:15]([F:17])[CH:16]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[F:31][C:32]([F:39])([F:38])[CH2:33][S:34](Cl)(=[O:36])=[O:35]>N1C=CC=CC=1>[C:1]([C:5]1[C:6]([O:29][CH3:30])=[C:7](/[CH:20]=[CH:21]/[C:22]2[N:27]=[CH:26][C:25]([NH:28][S:34]([CH2:33][C:32]([F:39])([F:38])[F:31])(=[O:36])=[O:35])=[CH:24][CH:23]=2)[CH:8]=[C:9]([C:11]2[C:12]([O:18][CH3:19])=[N:13][CH:14]=[C:15]([F:17])[CH:16]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 672865546-{(E)-2-[3-tert-butyl-5-(5-fluoro-2-methoxy-pyridin-3-yl)-2-methoxy-phenyl]-vinyl}-pyridin-3-ylamine

Produkt 1

HCID 672872432,2,2-trifluoro-ethanesulfonic acid (6-{(E)-2-[3-tert-butyl-5-(5-fluoro-2-methoxy-pyridin-3-yl)-2-methoxy-phenyl]-vinyl}-pyridin-3-yl)-amideAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

step 2—To a solution of 370 (90.0 mg, 0.221 mmol) in pyridine (3 mL) cooled to 0° C. was added 2,2,2 trifluoroethane sulfonyl chloride (40 μL, 0.364 mmol). After 20 min the reaction mixture was warmed to RT and stirred overnight. The reaction mixture was quenched with 30 mL of 1N HCl and thrice extracted with EtOAc (20 mL). The combined extracts were washed with sat'd. aq. CuSO4 (3×30 mL) and brine, dried (Na2SO4), filtered, and concentrated. The crude product was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (25 to 35% EtOAc) to afford 88.1 mg (72%) of 2,2,2-trifluoro-ethanesulfonic acid (6-{(E)-2-[3-tert-butyl-5-(5-fluoro-2-methoxy-pyridin-3-yl)-2-methoxy-phenyl]-vinyl}-pyridin-3-yl)-amide (372).

Aufarbeitung

  1. customThe reaction mixture was quenched with 30 mL of 1N HCl and thrice
  2. extractionextracted with EtOAc (20 mL)
  3. washThe combined extracts were washed with sat'd
  4. dry with materialaq. CuSO4 (3×30 mL) and brine, dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by SiO2 chromatography
  8. washeluting with an EtOAc/hexane gradient (25 to 35% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-47d89bf8e02949f4929d63b9a213bcd5
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273773B2

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