Cesium carbonate → 1,1-Dimethylethyl 5-(4-{[1-(1-methylethyl)-4-piperidinyl]methyl}-1-piperidinyl)-2-pyridinecarboxylate

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Reaction Steps

1-(1-Methylethyl)-4-(4-piperidinylmethyl)piperidine (may be prepared as described in Description 4) (0.25 g), 1,1-dimethylethyl 5-bromo-2-pyridinecarboxylate (may be prepared as described in Description 12) (0.29 g), BINAP (0.06 g) and Cs2CO3 (1.82 g) were added to toluene (50 ml) under argon and the reaction mixture degassed by sequential freezing in dry ice followed by warming to room temp under vacuum (3×). After stirring for 5 min Pd(OAc)2 (0.05 g) was added, degassed again, and the reaction mixture heated at 100° C. for 24 h. The reaction mixture was filtered and evaporated, after which chromatography (silica gel, eluting with methanol/dichloromethane, 0-20%) afforded the title compound (E4) as a yellow solid (0.25 g). MS electrospray (+ion) 424 (MNa+)

Provenance & Evidence