3-Chloropyridine → 4-(3-Pyridin-4-yl-[1,2,4]oxadiazol-5-ylmethoxy)-3,4,5,6-tetrahydro-2H-[1,3']bipyridinyl

HRID 221368

Reaktionsgleichung

CC(C)([O-])C.[Na+].Cl[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1.[NH:14]1[CH2:19][CH2:18][CH:17]([O:20][CH2:21][C:22]2[O:26][N:25]=[C:24]([C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)[N:23]=2)[CH2:16][CH2:15]1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:30]1[CH:31]=[CH:32][C:27]([C:24]2[N:23]=[C:22]([CH2:21][O:20][CH:17]3[CH2:18][CH2:19][N:14]([C:8]4[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=4)[CH2:15][CH2:16]3)[O:26][N:25]=2)=[CH:28][CH:29]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

Sodium tert-butoxide (86 mg, 900 μmol) was added to a solution of 3-chloropyridine (23 mg, 200 μmol), 4-[5-(piperidin-4-yloxymethyl)[1,2,4]oxadiazol-3-yl]pyridine (Preparation 17, 65 mg, 250 μmol), Pd2 dba3 (4 mg, 4 μmol) and 2,8,9-trisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (6 mg, 16 μmol) in toluene (3 ml) and the resulting mixture heated at 80° C. for 48 h. After cooling and filtering through celite, the solvent was removed and the residue purified by HPLC to afford the title compound: RT=2.64 min; m/z (ES+)=338.0 [M+H]+.

Aufarbeitung

temperatureAfter cooling
filtrationfiltering through celite
customthe solvent was removed
customthe residue purified by HPLC

Quellen und Nachweise

ORD-Eintrag: ord-9087b8d7f6164ccfa1636c0331c8aa98
Quelldatensatz: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08207147B2

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