Reaktionsgleichung
[CH2:1]([NH:3][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:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]2)=[CH:18][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.COCCOC>[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:23][CH:24]3[CH2:25][CH2:26][N:27]([C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31])[CH2:28][CH2:29]3)=[CH:20][CH:21]=2)=[CH:8][CH:7]=1)=[O:5])[CH3:2]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
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).
Quellen und Nachweise
- ORD-Eintrag
- ord-66a5bbf444464b77bb3ba2476c8661fe
- Quelldatensatz
- uspto-grants-2012_01
- Patentnummer
- US08101634B2
Verknüpfte Notizen
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