Water → Methyl 2'-(((2,4'-dichloro-2'-methyl-[1,1'-biphenyl]-4-yl)amino)methyl)-2-methyl-5'-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylate

HRID 2167135Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2167135
Br[C:2]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][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[CH3:19])=[C:8]([Cl:20])[CH:7]=1.[CH3:29][C:30]1[CH:31]=[C:32]([CH:37]=[CH:38][C:39]=1B1OC(C)(C)C(C)(C)O1)[C:33]([O:35][CH3:36])=[O:34].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:20][C:8]1[CH:7]=[C:6]([NH:5][CH2:4][C:3]2[CH:21]=[CH:22][C:23]([C:25]([F:28])([F:27])[F:26])=[CH:24][C:2]=2[C:39]2[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][C:30]=2[CH3:29])[CH:11]=[CH:10][C:9]=1[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[CH3:19]

Komponenten

8

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 110870242-Methyl-4-methoxycarbonylphenylboronic acid, pinacol esterHCID 86674206N-(2-bromo-4-(trifluoromethyl)benzyl)-2,4'-dichloro-2'-methyl-[1,1'-biphenyl]-4-amine

Produkt 1

HCID 71060183Methyl 2'-(((2,4'-dichloro-2'-methyl-[1,1'-biphenyl]-4-yl)amino)methyl)-2-methyl-5'-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylate

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-2′-methyl-[1,1′-biphenyl]-4-amine, prepared as described in Example 1, (500 mg, 1.0 mmol), methyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (339 mg, 1.2 mmol), Pd(dppf)Cl2 (84 mg, 0.1 mmol), and K2CO3 (283 mg, 2.0 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-369894951c154bd59ee0707b83d1a640
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045389B2

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