4-(Diethylcarbamoyl)phenylboronic Acid → 1-Methylethyl 4-[({4'-[(diethylamino)carbonyl]-4-biphenylyl}oxy)methyl]-1-piperidinecarboxylate

Participants

Reaction Steps

The title compound (39 mg, 34%) was prepared from {4-[(diethylamino)carbonyl]phenyl}boronic acid (44 mg, 0.2 mmol) and 1-methylethyl 4-{[(4-bromophenyl)oxy]methyl}-1-piperidinecarboxylate (prepared as in Example 9, Step 2, 71 mg, 0.2 mmol) 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 7.56 (d, 2H, J=8.4 Hz), 7.52 (d, 2H, J=8.8 Hz), 7.41 (d, 2H, J=8.2 Hz), 6.96 (d, 2H, J=8.8 Hz), 4.97-4.86 (m, 1H), 4.21 (bs, 2H), 3.84 (d, 2H, J=6.4 Hz), 3.56 (bs, 2H), 3.32 (bs, 2H), 2.84-2.74 (m, 2H), 2.05-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.38-1.06 (m, 14H); LRMS (ESI), m/z 453 (M+H).

Provenance & Evidence