Sodium Carbonate → 1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-[({4'-[(1-methylethyl)thio]-4-biphenylyl}oxy)methyl]piperidine

Participants

Reaction Steps

1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-[({4′-[(1-methylethyl)thio]-4-biphenylyl}oxy)methyl]piperidine (20 mg, 5%) was prepared as a white solid from {4-[(1-methylethyl)thio]phenyl}boronic acid (167 mg, 0.85 mmol), 4-{[(4-bromophenyl)oxy]methyl}-1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]piperidine (322 mg, 0.85 mmol), Pd(PPh3)2Cl2 (50 mg, 0.07 mmol), 2M Na2CO3 (5 mL) and DME (5 mL) in a manner similar to Example 21, Step 3. 1H NMR (400 MHz, CDCl3): δ 7.57-7.39 (m, 6H), 6.94 (d, 2H, J=8.9 Hz), 4.28-4.18 (m, 2H), 3.87 (d, 2H, J=6.4 Hz), 3.46-3.30 (m, 1H), 3.20-3.08 (m, 2H), 2.98-2.85 (m, 1H), 2.16-2.03 (m, 1H), 2.03-1.93 (m, 2H), 1.55-1.39 (m, 2H), 1.36-1.24 (m, 12H); LRMS (ESI), m/z 452 (M+H).

Provenance & Evidence