Ethyl 4-piperidinecarboxylate → Ethyl 1-(6-chloro-4-methyl-3-pyridinyl)piperidine-4-carboxylate

Reaction equation

CCOC(=O)C1CCNCC1.Cc1cc(Cl)ncc1Br>CC(=O)O.CC(=O)O.CC(C)(C)[O-].CC(C)Oc1cccc(OC(C)C)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.Cc1ccccc1.[Na+].[Pd]>CCOC(=O)C1CCN(c2cnc(Cl)cc2C)CC1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of diacetoxypalladium (10.87 mg, 0.05 mmol) and dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (45.2 mg, 0.10 mmol) dissolved in toluene (3 mL) was degassed and heated to 50°C for 30 minutes before adding ethyl piperidine-4-carboxylate (0.105 mL, 0.68 mmol), 5-bromo-2-chloro-4-methylpyridine (100 mg, 0.48 mmol) and sodium 2-methylpropan-2-olate (74.5 mg, 0.77 mmol) under nitrogen. The mixture was heated to 100°C for 2 hours. LCMS indicated little product so reaction abandoned.