Sodium Carbonate → 1-Methylethyl 4-({[4'-(methylsulfonyl)-4-biphenylyl]thio}methyl)-1-piperidinecarboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-methylethyl 4-{[(4-bromophenyl)thio]methyl}-1-piperidinecarboxylate (292 mg, 0.78 mmol), [4-(methylsulfonyl)phenyl]boronic acid (157 mg, 0.78 mmol), 2M Na2CO3 (2 mL), and Pd(PPh3)2Cl2 (200 mg, 0.28 mmol) in DME (8 mL) stirred at 80° C. for 3 h, then at ambient temperature overnight. The mixture was poured onto a Varian Chem Elut column, flushed with EtOAc, and the organics concentrated. The crude product was purified by chromatography on a silica gel column using 0 to 30% EtOAc/hexanes to give 105 mg (30%) of the title compound as a tan solid. 1H NMR (400 MHz, CDCl3): δ 7.98 (d, 2H, J=8.4 Hz), 7.73 (d, 2H, J=8.4 Hz), 7.51 (d, 2H, J=8.4 Hz), 7.38 (d, 2H, J=8.4 Hz), 4.89 (septet, 1H, J=6.2 Hz), 4.20-4.10 (m, 2H), 3.07 (s, 3H), 2.89 (d, 2H, J=6.8 Hz), 2.75-2.64 (m, 2H), 1.90-1.80 (m, 2H), 1.79-1.65 (m, 1H), 1.28-1.12 (m, 8H); LRMS (ESI), m/z 448 (M+H).

Provenance & Evidence