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

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+)

1. customthe reaction mixture degassed by sequential freezing in dry ice
2. additionwas added
3. customdegassed again
4. temperaturethe reaction mixture heated at 100° C. for 24 h
5. filtrationThe reaction mixture was filtered
6. customevaporated
7. washafter which chromatography (silica gel, eluting with methanol/dichloromethane, 0-20%)

ORD record

ord-e51c80b53ccb49b095f7e159614817d9

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07638631B2