Sodium Carbonate → 1-Methylethyl 4-[({4'-[(ethylamino)carbonyl]-4-biphenylyl}oxy)methyl]-1-piperidinecarboxylate

Participants

Reaction Steps

The title compound (11 mg, 26%) was prepared as a tan solid from {4-[(ethylamino)carbonyl]phenyl}boronic acid (19 mg, 0.1 mmol), 1-methylethyl 4-{[(4-bromophenyl)oxy]methyl}-1-piperidinecarboxylate (prepared as in Example 9, Step 2, 36 mg, 0.1 mmol), Pd(PPh3)2Cl2 (10 mg, 0.01 mmol), 2M Na2CO3 (1 mL) and DME (1 mL) in a manner similar to Example 21, Step 3, and worked up in a manner similar to Example 9, Step 3. 1H NMR (400 MHz, CDCl3): δ 7.80 (d, 2H, J=8.4 Hz), 7.60 (d, 2H, J=8.6 Hz), 7.54 (d, 2H, J=8.8 Hz), 6.96 (d, 2H, J=8.8 Hz), 6.09 (t, 1 H, J=5.4 Hz), 4.98-4.84 (m, 1H), 4.20 (bs, 2H), 3.85 (d, 2H, J=6.4 Hz), 3.61-3.41 (m, 2H), 2.87-2.71 (m, 2H), 2.05-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.32-1.13 (m, 11H); LRMS (ESI), m/z 425 (M+H).

Provenance & Evidence