3-Bromo-2-chloropyridine → 3'-[(3-Bromopyridin-2-yl)amino]-6-methyl-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide

HRID 77726

Reaktionsgleichung

Reaktionsgleichung von HRID 77726
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)=[O:16])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Br:28][C:29]1[C:30](Cl)=[N:31][CH:32]=[CH:33][CH:34]=1>CO>[Br:28][C:29]1[C:30]([NH:1][C:2]2[CH:3]=[C:4]([C:8]3[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]([C:15]([NH:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:25])([F:26])[F:27])[CH:19]=4)=[O:16])[CH:9]=3)[CH:5]=[CH:6][CH:7]=2)=[N:31][CH:32]=[CH:33][CH:34]=1

Komponenten

4

Edukt 2

HCID 6933243-Bromo-2-chloropyridineHCID 690436683'-Amino-6-methyl-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide

Produkt 1

HCID 692684343'-[(3-Bromopyridin-2-yl)amino]-6-methyl-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamideAusbeute 40,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A mixture of 3′-amino-6-methyl-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide (150 mg, 0.41 mmol) and 3-bromo-2-chloropyridine (90 mg, 0.47 mmol) was heated neat to 180° C. in an oil bath. The temperature was increased to 200° C., and then heating was discontinued and the reaction mixture was allowed to stir for 72 h. The resulting solid was dissolved in methanol and purified by flash column chromatography (eluting with a gradient of 0-40% ethyl acetate in hexanes) to afford product (87 mg, 39%).

Aufarbeitung

  1. temperatureThe temperature was increased to 200° C.
  2. temperatureheating
  3. custompurified by flash column chromatography (
  4. washeluting with a gradient of 0-40% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b898b2ff2a2a4343b26a02e88c8107ab
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841318B2

Verknüpfte Notizen

Wird geladen…