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

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Reaction Conditions

Reaction Steps

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]+.

Provenance & Evidence