Water → 3-Fluoro-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

HRID 2181893

Reaktionsgleichung

F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]([NH:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH3:16].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:8][C:6]1[CH:7]=[CH:2][C:3]2[C:9]3[C:10]([CH:15]([CH3:16])[N:17]([S:18]([C:21]4[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=4)(=[O:19])=[O:20])[C:4]=2[CH:5]=1)=[CH:11][CH:12]=[CH:13][CH:14]=3

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

N-[1-(2′,4′-Difluoro-1,1′-biphenyl-2-yl)ethyl]4-methoxybenzenesulfonamide (347 mg, 0.86 mmol) was dissolved in anhydrous N,N-dimethylformamide (2 mL) and potassium carbonate (238 mg, 1.72 mmol) was added as a solid in one portion. The mixture was heated at 100° C. with stirring until a single product had formed as gauged by LCMS (5-6 hours). Water (10 mL) was added and a white solid precipitated from the cloudy solution. The mixture was allowed to stand until the solution was clear, and the precipitated solid was filtered and washed with additional water to afford the desired compound (324 mg, 98%) as a white solid, m.p. 137.5-139° C.;

Aufarbeitung

customhad formed
customas gauged by LCMS (5-6 hours)
customa white solid precipitated from the cloudy solution
filtrationthe precipitated solid was filtered
washwashed with additional water

Quellen und Nachweise

ORD-Eintrag: ord-8f7a79e8c94445db8000f2092601fa74
Quelldatensatz: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06894061B2

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