Azidotrimethylsilane → ethyl 2-(9-azido-7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-yl)acetate
Reaktionsgleichung
[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][C:7]3[C:8]([F:25])=[CH:9][C:10]([O:23][CH3:24])=[CH:11][C:12]=3[C:13]2([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])O)=[CH:4][CH:3]=1.[N:26]([Si](C)(C)C)=[N+:27]=[N-:28].C([O+]([B-](F)(F)F)CC)C>C1(C)C=CC=CC=1>[N:26]([C:13]1([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:12]2[CH:11]=[C:10]([O:23][CH3:24])[CH:9]=[C:8]([F:25])[C:7]=2[O:6][C:5]2[C:14]1=[CH:15][C:2]([Br:1])=[CH:3][CH:4]=2)=[N+:27]=[N-:28]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of ethyl 2-(7-bromo-4-fluoro-9-hydroxy-2-methoxy-9H-xanthen-9-yl)acetate (1.0 g, 2.432 mmol) in toluene (25 ml) was added azidotrimethylsilane (0.560 g, 4.86 mmol). The solution was cooled to 0° C. and (diethyloxonio)trifluoroborate (0.308 ml, 2.432 mmol) was added drop wise. The mixture was stirred overnight at RT. The solution was quenched with MeOH (10 ml) and diluted with EtOAc. The organic phase was separated, washed with saturated aqueous sodium bicarbonate solution and brine, and then concentrated to afford crude ethyl 2-(9-azido-7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-yl)acetate (1 g, 2.292 mmol, 94% yield).
Aufarbeitung
- customThe solution was quenched with MeOH (10 ml)
- additiondiluted with EtOAc
- customThe organic phase was separated
- washwashed with saturated aqueous sodium bicarbonate solution and brine
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-bca0c6b09682426fb96c40b6b3296e02
- Quelldatensatz
- uspto-grants-2013_07
- Patentnummer
- US08497264B2
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