Water → Ethyl 3-(5-(2-(((3',4'-dichloro-2-fluoro-[1,1'-biphenyl]-4-yl)amino)methyl)-5-fluorophenyl)picolinamido)propanoate

HRID 405172Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 405172
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[C:17]2[CH:18]=[CH:19][C:20]([C:23]([NH:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:24])=[N:21][CH:22]=2)=[CH:4][C:3]=1[F:33].[Cl:34][C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][C:40]=1[Cl:41].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:34][C:35]1[CH:36]=[C:37]([C:2]2[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=3[C:17]3[CH:18]=[CH:19][C:20]([C:23]([NH:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:24])=[N:21][CH:22]=3)=[CH:4][C:3]=2[F:33])[CH:38]=[CH:39][C:40]=1[Cl:41]

Komponenten

8

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27343303,4-Dichlorobenzeneboronic acidHCID 71059826Ethyl 3-(5-(2-(((4-bromo-3-fluorophenyl)amino)methyl)-5-fluorophenyl)picolinamido)propanoate

Produkt 1

HCID 71059960Ethyl 3-(5-(2-(((3',4'-dichloro-2-fluoro-[1,1'-biphenyl]-4-yl)amino)methyl)-5-fluorophenyl)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

Ethyl 3-(5-(2-(((4-bromo-3-fluorophenyl)amino)methyl)-5-fluorophenyl)picolinamido)propanoate (100 mg, 0.19 mmol), (3,4-dichlorophenyl)boronic acid (44 mg, 0.23 mmol), Pd(dppf)Cl2 (21 mg, 0.03 mmol), and K2CO3 (53 mg, 0.39 mmol) were dissolved in 1,4-dioxane (4 mL) and water (1 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), concentrated and purified via column chromatography to yield the title compound.

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified via column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b66eda5aa4814806bcae1fc934adb6c8
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748624B2

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