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

HRID 405218Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 405218
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([CH:38]=O)=[C:20]([C:22]2[CH:23]=[CH:24][C:25]([C:28]([NH:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:29])=[N:26][CH:27]=2)[CH:21]=1.[F:40][C:41]1[CH:42]=[C:43]([C:48]2[CH:53]=[CH:52][C:51]([NH2:54])=[CH:50][CH:49]=2)[CH:44]=[CH:45][C:46]=1[F:47]>CC(O)=O.C(Cl)Cl.C([O-])(O)=O.[Na+]>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:38][NH:54][C:51]2[CH:50]=[CH:49][C:48]([C:43]3[CH:44]=[CH:45][C:46]([F:47])=[C:41]([F:40])[CH:42]=3)=[CH:53][CH:52]=2)=[C:20]([C:22]2[CH:23]=[CH:24][C:25]([C:28]([NH:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:29])=[N:26][CH:27]=2)[CH:21]=1

Komponenten

7

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 610262874-(3,4-Difluorophenyl)anilineHCID 86674246Ethyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate

Produkt 1

HCID 71059933Ethyl 3-(5-(5-chloro-2-(((3',4'-difluoro-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidKatalysatorHCID 6344DichloromethaneLösungsmittel2×HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

Solid NaBH(OAc)3 (116 mg, 0.55 mmol) was added to a DCM solution (1 mL) of ethyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate (95 mg, 0.27 mmol), 3′,4′-difluoro-[1,1′-biphenyl]-4-amine (73 mg, 0.36 mmol), and 1 drop of AcOH and the resulting mixture was stirred at room temperature. After 3 h the resulting mixture diluted with DCM and saturated aqueous NaHCO3 and the layers were separated. The organic phase was washed with brine, dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Aufarbeitung

  1. customthe layers were separated
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified via column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c9ed4ab643ee4801b318f8a051da30ff
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748624B2

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