Bromine → 4-(3-bromo-2-{2-[(2R)-2-methylpyrrolidin-1-yl]ethyl}-1-benzofuran-5-yl)benzonitrile
Reaktionsgleichung
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]3[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=3)=[CH:14][C:12]=2[CH:13]=1.[Br:26]Br.[O-]S([O-])=O.[Na+].[Na+]>C(O)(C(F)(F)F)=O>[Br:26][C:13]1[C:12]2[CH:14]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]([C:22]#[N:23])=[CH:24][CH:25]=3)[CH:16]=[CH:17][C:11]=2[O:10][C:9]=1[CH2:8][CH2:7][N:3]1[CH2:4][CH2:5][CH2:6][C@H:2]1[CH3:1]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 25 °C
Versuchsvorschrift
The product from Example 1D (2.5 g (5.2 mmol) and trifluoroacetic acid (40 mL) (TFA) were combined and stirred at 25° C. for 10 min. The mixture was slowly treated with a solution of Br2 (450 μL, 7.8 mmol) in TFA (10 mL). The mixture was allowed to stir at 25° C. for 1 h and then treated with saturated aqueous Na2SO3. The mixture was concentrated and redissolved in 50 mL ethyl acetate. The organic phase was washed with 1M NaOH, dried, and concentrated under reduced pressure to provide the title compound (2.1 g, 97% yield). 1HNMR (300 MHz, CD3OD) δ 1.16 (d, 3H, J=6.1 Hz), 1.42 (m, 1H), 1.78 (m, 2H), 1.98 (m, 1H), 2.32 (m, 1H), 2.50 (m, 2H), 3.11 (m, 2H), 3.28 (m, 2H), 7.58-7.70 (m, 3H), 7.82 (m, 4H); MS (ESI) m/e 409 (M+H)+.
Aufarbeitung
- stirringto stir at 25° C. for 1 h
- concentrationThe mixture was concentrated
- dissolutionredissolved in 50 mL ethyl acetate
- washThe organic phase was washed with 1M NaOH
- customdried
- concentrationconcentrated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-cb1fbaea42144b67ac62a68d81fde0e3
- Quelldatensatz
- uspto-grants-2009_05
- Patentnummer
- US07538138B2
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