Nitrogen → 3-[[2-Fluoro-5-(3-fluorophenyl)-3-methyl-phenyl]methylamino]-2,4-dimethyl-phenol

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Reaktionsgleichung

[F:1][C:2]1[C:19]([CH3:20])=[CH:18][C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=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.N#N>C1COCC1>[F:1][C:2]1[C:19]([CH3:20])=[CH:18][C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=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)-3-methyl-benzamide (270 mg, 0.7 mmol, 1.0 eq) in THF (15 mL) was added a solution of BH3 (1M in THF, 4.4 mL, 4.4 mmol, 6.0 eq) dropwise under N2. The reaction mixture was heated at 60° C. overnight. After cooling, the resulting mixture was quenched by the addition of water and the aqueous layer extracted with EtOAc. The organic extract was washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by column chromatography (petroleum ether: EtOAc, 30:1 to 20:1) to give the title compound as a colorless oil (106 mg, 41%).

Aufarbeitung

temperatureAfter cooling
customthe resulting mixture was quenched by the addition of water
extractionthe aqueous layer extracted with EtOAc
extractionThe organic extract
washwas washed with water and brine
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated in vacuo
customThe residue was purified by column chromatography (petroleum ether: EtOAc, 30:1 to 20:1)

Quellen und Nachweise

ORD-Eintrag: ord-edad71d85406447fa9639d32dda7f2b8
Quelldatensatz: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09249085B2

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