Water → Ethyl 3-(5-(2-(((2-chloro-2'-methyl-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)amino)methyl)-5-(trifluoromethyl)phenyl)picolinamido)propanoate

HRID 405161

Reaktionsgleichung

Reaktionsgleichung von HRID 405161
Br[C:2]1[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][C:3]=1[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=2[CH3:22])=[C:8]([Cl:23])[CH:7]=1.CC1(C)C(C)(C)OB([C:40]2[CH:41]=[CH:42][C:43]([C:46]([NH:48][CH2:49][CH2:50][C:51]([O:53][CH2:54][CH3:55])=[O:52])=[O:47])=[N:44][CH:45]=2)O1.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:23][C:8]1[CH:7]=[C:6]([NH:5][CH2:4][C:3]2[CH:24]=[CH:25][C:26]([C:28]([F:31])([F:30])[F:29])=[CH:27][C:2]=2[C:40]2[CH:41]=[CH:42][C:43]([C:46]([NH:48][CH2:49][CH2:50][C:51]([O:53][CH2:54][CH3:55])=[O:52])=[O:47])=[N:44][CH:45]=2)[CH:11]=[CH:10][C:9]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=1[CH3:22]

Komponenten

8

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 71059832Ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoateHCID 86674211N-(2-bromo-4-(trifluoromethyl)benzyl)-2-chloro-2'-methyl-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-amine

Produkt 1

HCID 86674252Ethyl 3-(5-(2-(((2-chloro-2'-methyl-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)amino)methyl)-5-(trifluoromethyl)phenyl)picolinamido)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

N-(2-bromo-4-(trifluoromethyl)benzyl)-2-chloro-2′-methyl-4′-(trifluoromethyl)-[1,1′-biphenyl]-4-amine (3.9 g, 7.5 mmol), ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate, prepared as in STEP A above, (3.2 g, 6.6 mmol), Pd(dppf)Cl2 (611 mg, 0.7 mmol), and K2CO3 (2.1 g, 14.9 mmol) were dissolved in 1,4-dioxane (60 mL) and water (15 mL) and the resulting mixture was heated to 80° C. After 16 h the resulting mixture was cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (Na2SO4), and dry packed onto silica gel. Column chromatography yielded the title compound.

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. customdry

Quellen und Nachweise

ORD-Eintrag
ord-d8195f3cbe8f4fc99e812d7273ddbbd2
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748624B2

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