m-Fluorobenzenethiol → 1-(4-Fluoro-2-methylphenyl)-6-(3-fluorophenylthio)phthalazine

HRID 454868

Reaktionsgleichung

Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[CH3:19])=[N:7][N:6]=[CH:5]2.[F:20][C:21]1[CH:22]=[C:23]([SH:27])[CH:24]=[CH:25][CH:26]=1>CCN(CC)CC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(P[C-]1C=CC=C1)(C)C.[C-]1(PC(C)C)C=CC=C1.[Fe+2]>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:8]2[C:9]3[C:4](=[CH:3][C:2]([S:27][C:23]4[CH:24]=[CH:25][CH:26]=[C:21]([F:20])[CH:22]=4)=[CH:11][CH:10]=3)[CH:5]=[N:6][N:7]=2)=[C:13]([CH3:19])[CH:14]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A mixture of 6-chloro-1-(4-fluoro-2-methylphenyl)phthalazine (0.197 g, 0.72 mmol), palladium(II) acetate (0.011 g, 0.049 mmol), 1,1′-bis(isopropylphosphino)ferrocene (0.022 g, 0.053 mmol) and 3-fluorothiophenol (0.080 ml, 0.95 mmol) in 2 mL of Et3N was sealed in a glass tube purged with argon and heated at 100° C. in an oil bath for 17 h. The reaction mixture was cooled to RT and diluted with MeOH. The solution was evaporated onto silica gel and purified by flash chromatography (ISCO 80 g column, eluting with 15-45% EtOAc in hexanes) to give the title compound as a white amorphous solid. MS (ESI, pos. ion) m/z: M+1=365.1

Aufarbeitung

customwas sealed in a glass tube
custompurged with argon
temperatureThe reaction mixture was cooled to RT
additiondiluted with MeOH
customThe solution was evaporated onto silica gel
custompurified by flash chromatography (ISCO 80 g column, eluting with 15-45% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-38a781dbc886467fa860b8024e980be1
Quelldatensatz: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08497269B2

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