Reaktionsgleichung
Cl[C:2]1[C:7]2[CH:8]=[C:9]([S:11]([O-:13])=[O:12])[S:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[Li+].[F:15][C:16]([F:26])([F:25])[C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1.[C:27]([O:31][C:32]([N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28]>C(#N)C>[C:27]([O:31][C:32]([N:34]1[CH2:39][CH2:38][N:37]([C:2]2[C:7]3[CH:8]=[C:9]([S:11]([CH2:21][C:20]4[CH:23]=[CH:24][C:17]([C:16]([F:26])([F:25])[F:15])=[CH:18][CH:19]=4)(=[O:13])=[O:12])[S:10][C:6]=3[CH:5]=[CH:4][N:3]=2)[CH2:36][CH2:35]1)=[O:33])([CH3:30])([CH3:28])[CH3:29]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Lithium 4-chlorothieno[3,2-c]pyridine-2-sulfinate (0.44 mmol) was treated with 4-(trifluoromethyl)benzylbromide (0.59 mmol) as described in Method P above and then reacted further with tert-butyl-piperazine-1-carboxylate as described in Method QF. Yield 0.02 g (16% over two steps). Beige solid. 1H NMR (300 MHz, CDCl3) δ 8.16 (d, J=6 Hz 1H), 7.53-7.61 (d, J=9 Hz 2H), 7.49 (s, 1H), 7.26-7.36 (m, 4H), 4.51 (s, 2H), 3.49-3.60 (m, 4H), 3.36-3.49 (m, 4H), 1.49 (s, 9H); MS (ESI+) for C24H26F3N3O4S2 m/z 542 (M+H)+. HPLC 71%, RT 4.07 min (ACE3 C8 50×4 mm, 5-50% acetonitrile in 3 min).
Quellen und Nachweise
- ORD-Eintrag
- ord-490fcfccfbf140eab6f367ade7f5ed72
- Quelldatensatz
- uspto-grants-2011_05
- Patentnummer
- US07943639B2
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