2-Fluoro-5-(3-fluorophenyl)-N-(3-hydroxy-2,6-dimethyl-phenyl)benzamide → 3-[[2-Fluoro-5-(3-fluorophenyl)phenyl]methylamino]-2,4-dimethyl-phenol

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Reaktionsgleichung

[F:1][C:2]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]([OH:14])[C:8]=1[CH3:15])=O>C1COCC1>[F:1][C:2]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)=[CH:16][C:3]=1[CH2:4][NH:6][C:7]1[C:8]([CH3:15])=[C:9]([OH:14])[CH:10]=[CH:11][C:12]=1[CH3:13]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To a solution of 2-fluoro-5-(3-fluorophenyl)-N-(3-hydroxy-2,6-dimethyl-phenyl)benzamide (400 mg, 1.13 mmol, 1.0 eq) in THF under N2 was added dropwise a solution of BH3 (5.65 mL, 1M in THF, 5.65 mmol, 5.0 eq). The reaction mixture was heated to 60° C. and stirred under N2 for 3 h. After cooling, the resulting mixture was quenched by addition of 1 M HCl and water and the aqueous layer extracted with EtOAc. The organic extract was dried (Na2SO4), filtered, evaporated in vacuo and purified by column chromatography (EtOAc:petroleum ether, 0:1 to 1:4) to give the title product as yellow oil (340 mg, 89%).

Aufarbeitung

temperatureAfter cooling
customthe resulting mixture was quenched by addition of 1 M HCl and water
extractionthe aqueous layer extracted with EtOAc
extractionThe organic extract
dry with materialwas dried (Na2SO4)
filtrationfiltered
customevaporated in vacuo
custompurified by column chromatography (EtOAc:petroleum ether, 0:1 to 1:4)

Quellen und Nachweise

ORD-Eintrag: ord-835ae528c7cf4b31abad7b32b4155ac5
Quelldatensatz: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09249085B2

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