Trifluoro-methanesulfonic acid 4-methyl-6-(4-trifluoromethylphenyl)-pyrimidin-2-yl ester → N-tert-Butyl-3-{6-[4-methyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-pyridin-2-yl}-benzenesulfonamide

HRID 1989743Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1989743
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:5]=[C:4](OS(C(F)(F)F)(=O)=O)[N: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[CH:45]=[CH:44][CH:43]=[C:42]([C:4]3[N:3]=[C:2]([CH3:1])[CH:7]=[C:6]([C:8]4[CH:9]=[CH:10][C:11]([C:14]([F:15])([F:16])[F:17])=[CH:12][CH:13]=4)[N:5]=3)[N:41]=2)[CH:35]=1)(=[O:33])=[O:32])([CH3:29])([CH3:27])[CH3:28]

Komponenten

4

Edukt 2

HCID 57468692Trifluoro-methanesulfonic acid 4-methyl-6-(4-trifluoromethylphenyl)-pyrimidin-2-yl esterHCID 60209340HCID 60209340, Verbindung

Produkt 1

HCID 57469110N-tert-Butyl-3-{6-[4-methyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-pyridin-2-yl}-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A stirred mixture of trifluoro-methanesulfonic acid 4-methyl-6-(4-trifluoromethylphenyl)-pyrimidin-2-yl ester (Example A.62) (0.418 g, 1.08 mmol), N-tert-butyl-3-(6-tributylstannanyl-pyridin-2-yl)-benzenesulfonamide (Example F.6) (0.570 g, 0.98 mmol), tetrakis(triphenyl-phosphine)palladium (0.057 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 (260 mg, 50%). MS (ISP) 527.3 [(M+H)+]; mp>250° 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-595b4311374c4181b6f402e21a043298
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07642264B2

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