Potassium Carbonate → 2-[4-(5-Pyridin-4-yl-pyrazol-1-yl)-phenoxymethyl]-quinoline

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Reaktionsgleichung

[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[N:10]=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:26][C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=1>CC(C)=O.[Cl-].[Na+].O>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:26][C:27]4[CH:36]=[CH:35][C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[N:28]=4)=[CH:14][CH:13]=3)[N:10]=[CH:9][CH:8]=2)=[CH:5][CH:6]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To a solution of 4-(5-Pyridin-4-yl-pyrazol-1-yl)-phenol (82 mg) in acetone was added potassium carbonate (153 mg) and 2-Chloromethyl-quinoline (95 mg) and the reaction mixture heated at 60° C. for 18 h. The reaction mixture was poured into brine and extracted with ethyl acetate, dried magnesium sulfate, filtered and concentrated. Purification via combiflash MPLC provided the title compound (91 mg). 1H NMR (400 MHz, CDCl3) δ 8.51 (m, 2H), 8.20 (d, J=8.7 Hz, 1H), 8.06 (d, J=8.7 Hz, 1H), 7.83 (d, J=7.1 Hz, 1H), 7.74 (m, 2H), 7.65 (d, J=8.7 Hz, 1H), 7.57 (m, 1H), 7.20 (d, J=8.7 Hz, 2H), 7.09 (d, J=5.8 Hz, 2H), 7.02 (d, J=9.1 Hz, 2H), 6.60 (d, J=1.7 Hz, 1H), 5.39 (s, 2H); MS: (M+H m/z=379.0).

Aufarbeitung

extractionextracted with ethyl acetate, dried magnesium sulfate
filtrationfiltered
concentrationconcentrated
customPurification via combiflash MPLC

Quellen und Nachweise

ORD-Eintrag: ord-836547c216364c8880f9567c6fbc831e
Quelldatensatz: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07825254B2

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