4-(Diethylcarbamoyl)phenylboronic Acid → 1-Methylethyl 4-[({4'-[(diethylamino)carbonyl]-4-biphenylyl}oxy)methyl]-1-piperidinecarboxylate
Reaction equation
[CH2:1]([N:3]([CH2:15][CH3:16])[C:4]([C:6]1[CH:11]=[CH:10][C:9](B(O)O)=[CH:8][CH:7]=1)=[O:5])[CH3:2].Br[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]2[CH2:31][CH2:30][N:29]([C:32]([O:34][CH:35]([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]2)=[CH:20][CH:19]=1>>[CH2:1]([N:3]([CH2:15][CH3:16])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:18]2[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH:26]3[CH2:27][CH2:28][N:29]([C:32]([O:34][CH:35]([CH3:37])[CH3:36])=[O:33])[CH2:30][CH2:31]3)=[CH:22][CH:23]=2)=[CH:8][CH:7]=1)=[O:5])[CH3:2]Participants
3
Procedure
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).
Sources & evidence
- ORD record
- ord-136e953db1d0428b8d1fce1a8c0ed5bd
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08101634B2
Reaction notes
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