Water → HCID 71060009, Verbindung

HRID 405145

Reaktionsgleichung

Reaktionsgleichung von HRID 405145
Br[C:2]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][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]([Cl:18])=[CH:14][C:13]=2[Cl:19])=[CH:8][CH:7]=1.CC1(C)C(C)(C)OB([C:36]2[CH:37]=[CH:38][C:39]([C:42]([NH:44][CH2:45][CH2:46][C:47]([O:49][CH2:50][CH3:51])=[O:48])=[O:43])=[N:40][CH:41]=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:19][C:13]1[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=1[C:9]1[CH:10]=[CH:11][C:6]([NH:5][CH2:4][C:3]2[CH:20]=[CH:21][C:22]([C:24]([F:27])([F:26])[F:25])=[CH:23][C:2]=2[C:36]2[CH:37]=[CH:38][C:39]([C:42]([NH:44][CH2:45][CH2:46][C:47]([O:49][CH2:50][CH3:51])=[O:48])=[O:43])=[N:40][CH:41]=2)=[CH:7][CH:8]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 71059832Ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoateHCID 86674248N-(2-bromo-4-(trifluoromethyl)benzyl)-2',4'-dichloro-[1,1'-biphenyl]-4-amine

Produkt 1

HCID 71060009HCID 71060009, Verbindung

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′,4′-dichloro-[1,1′-biphenyl]-4-amine (386 mg, 0.8 mmol), ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate, prepared as in step a, (424 mg, 1.2 mmol), Pd(dppf)Cl2 (67 mg, 0.1 mmol), and K2CO3 (225 mg, 1.6 mmol) were dissolved in 1,4-dioxane (8 mL) and water (2 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-05d027eacce74e70839d2ea5be5f8ec1
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748624B2

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