HCID 60209340, Verbindung → HCID 67392744, Verbindung

HRID 906300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 906300
[CH3:1][C:2]1[N:7]=[C:6](OS(C(F)(F)F)(=O)=O)[CH:5]=[C:4]([C:16]2[CH:17]=[N:18][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:21]=2)[CH:3]=1.[C:26]([NH:30][S:31]([C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([Sn](CCCC)(CCCC)CCCC)[N:41]=2)[CH:35]=1)(=[O:33])=[O:32])([CH3:29])([CH3:28])[CH3:27]>C1(C)C=CC=CC=1>[C:26]([NH:30][S:31]([C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([C:40]2[N:41]=[C:42]([C:6]3[CH:5]=[C:4]([C:16]4[CH:17]=[N:18][C:19]([C:22]([F:23])([F:24])[F:25])=[CH:20][CH:21]=4)[CH:3]=[C:2]([CH3:1])[N:7]=3)[CH:43]=[CH:44][CH:45]=2)[CH:35]=1)(=[O:32])=[O:33])([CH3:29])([CH3:27])[CH3:28]

Komponenten

4

Edukt 2

HCID 60209340HCID 60209340, VerbindungHCID 86624636HCID 86624636, Verbindung

Produkt 1

HCID 67392744HCID 67392744, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A stirred mixture of trifluoro-methanesulfonic acid 6′-methyl-6-trifluoromethyl-[3,4′]bipyridinyl-2′-yl ester (Example A.5) (0.193 g, 0.5 mmol), N-tert-butyl-3-(6-tributylstannanyl-pyridin-2-yl)-benzenesulfonamide (Example C.2) (0.264 g, 0.455 mmol), tetrakis(triphenyl-phosphine)palladium (0.029 g, 5 mol %) in toluene (5 mL) was heated under reflux conditions for 18 h. Cooled to rt, extracted with ethyl acetate and water, dried the organic layer over Na2SO4. Removal of the solvent in vacuum left a crude product which was purified by silica gel column chromatography with n-heptane/ethyl acetate to give the title compound after trituration with diethyl ether as a white solid (110 mg, 42%). MS (ISP) 527.0 [(M+H)+]; mp 187-188° C.

Aufarbeitung

  1. temperaturewas heated under reflux conditions for 18 h
  2. extractionextracted with ethyl acetate and water
  3. dry with materialdried the organic layer over Na2SO4
  4. customRemoval of the solvent in vacuum
  5. waitleft a crude product which
  6. customwas purified by silica gel column chromatography with n-heptane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-509f5eed8e894cad9f575579480aa107
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012986B2

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