N-(2,6-Difluoro-3-hydroxy-phenyl)-5-(3-fluorophenyl)-2-methyl-benzamide → 2,4-Difluoro-3-[[5-(3-fluorophenyl)-2-methyl-phenyl]methyl amino]phenol

HRID 1771597Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1771597
[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]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)[CH:15]=[CH:14][C:13]=1[CH3:25]>C1COCC1>[F:1][C:2]1[C:3]([NH:10][CH2:11][C:12]2[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=3)[CH:15]=[CH:14][C:13]=2[CH3:25])=[C:4]([F:9])[CH:5]=[CH:6][C:7]=1[OH:8]

Komponenten

3

Edukt 1

HCID 89443775N-(2,6-Difluoro-3-hydroxy-phenyl)-5-(3-fluorophenyl)-2-methyl-benzamide

Produkt 1

HCID 894454532,4-Difluoro-3-[[5-(3-fluorophenyl)-2-methyl-phenyl]methyl amino]phenolAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a solution of N-(2,6-difluoro-3-hydroxy-phenyl)-5-(3-fluorophenyl)-2-methyl-benzamide (150 mg, 0.42 mmol, 1.0 eq) in THF (5 mL) was added dropwise a solution of BH3 (1 M in THF, 3 mL, 3 mmol, 7 eq). The reaction was heated at 55° C. under N2 for 2 h, and then quenched by the addition of 1M HCl. The aqueous layer was extracted with EtOAc and the combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo to give compound the title compound as a solid (124 mg, 86%).

Aufarbeitung

  1. customquenched by the addition of 1M HCl
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washthe combined organic extracts were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-609720c0244f485caa5715ccb40148f8
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249085B2

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