4-(Butylaminocarbonyl)phenylboronic acid → 1-Methylethyl 4-[({4'-[(butylamino)carbonyl]-4-biphenylyl}oxy)methyl]-1-piperidinecarboxylate

Participants

Reaction Steps

The title compound (26 mg, 23%) was prepared from {4-[(butylamino)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 7.80 (d, 2H, J=8.6 Hz), 7.60 (d, 2H, J=8.6 Hz), 7.54 (d, 2H, J=8.9 Hz), 6.96 (d, 2H, J=8.8 Hz), 6.11 (t, 1H, J=5.7 Hz), 5.01-4.83 (m, 1H), 4.21 (bs, 2H), 3.85 (d, 2H, J=6.4 Hz), 3.53-3.39 (m, 2H), 2.83-2.73 (m, 2H), 2.05-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.67-1.55 (m, 2H), 1.46-1.37 (m, 2H), 1.36-1.25 (m, 2H), 1.24 (d, 6H, J=6.2 Hz), 0.96 (t, 3H, J=7.3 Hz); LRMS (ESI), m/z 453 (M+H).

Provenance & Evidence