N-(2,6-Difluoro-3-hydroxy-phenyl)-3-(3-fluorophenyl)benzamide → 2,4-Difluoro-3-[[3-(3-fluorophenyl)phenyl]methylamino]phenol

HRID 1771607Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1771607
[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[NH:10][C:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)[CH:13]=1>C1COCC1>[F:1][C:2]1[C:3]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=3)[CH:13]=2)=[C:4]([F:9])[CH:5]=[CH:6][C:7]=1[OH:8]

Komponenten

3

Edukt 1

HCID 89443548N-(2,6-Difluoro-3-hydroxy-phenyl)-3-(3-fluorophenyl)benzamide

Produkt 1

HCID 894442752,4-Difluoro-3-[[3-(3-fluorophenyl)phenyl]methylamino]phenolAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of N-(2,6-difluoro-3-hydroxy-phenyl)-3-(3-fluorophenyl)benzamide (310 mg, 0.9 mmol, 1.0 eq) in THF (5 mL) was added BH3 (5.4 mL, 1M in THF, 5.4 mmol, 6.0 eq) and the reaction heated at 60° C. overnight. The reaction mixture was quenched with water and extracted with EtOAc. The organic extract was washed with water and brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by column chromatography (petroleum ether:EtOAc 1:0 to 10:1) to give the title compound as an oil (255 mg, 86%).

Aufarbeitung

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography (petroleum ether:EtOAc 1:0 to 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-ac1196616a1e4c9ba367166cfd7a3fa3
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249085B2

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