Reaktion #420094

Reaktionsgleichung

triethyl amine

tert-butyl 4-vinyl-1H-imidazole-1-carboxylate

3-(4-bromophenoxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-6-ol

→

(E)-3-(4-(2-(1H-imidazol-4-yl)vinyl)phenoxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-6-ol

Ausbeute 15.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe system was flushed with nitrogen
2. 2
   TemperaturThe mixture was cooled to room temperature
3. 3
   workup.ADDITIONdiluted with DCM and sat. aq. NH4Cl
4. 4
   SonstigeThe organic layer was collected (phase separator)
5. 5
   Einengenconcentrated in vacuo
6. 6
   Sonstigepurified by reverse phase HPLC (basic condition, 0.1% NH4OH in 1-100% CH3CN/H2O)

Vorschrift

To a microwave vial containing 3-(4-bromophenoxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-6-ol (20 mg, 0.05 mmol) in DMF (2 mL) was added triethyl amine (0.202 mL, 1.45 mmol), tert-butyl 4-vinyl-1H-imidazole-1-carboxylate (28.2 mg, 0.15 mmol) and Pd(PPh3)2Cl2 (3.40 mg, 4.84 μmol). The system was flushed with nitrogen and heated at 150° C. for 1 h under microwave irradiation. The mixture was cooled to room temperature and diluted with DCM and sat. aq. NH4Cl. The organic layer was collected (phase separator), concentrated in vacuo and purified by reverse phase HPLC (basic condition, 0.1% NH4OH in 1-100% CH3CN/H2O) to afford (E)-3-(4-(2-(1H-imidazol-4-yl)vinyl)phenoxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-6-ol (3 mg, 7.03 μmol, 15% yield) as a white solid. 1H NMR (400 MHz, CD3OD) δ ppm=7.57 (s, 1H), 7.43 (d, J=8.59 Hz, 2H), 7.30 (d, J=8.59 Hz, 2H), 6.96-7.14 (m, 3H), 6.74-6.96 (m, 4H), 6.53-6.74 (m, 3H). LC/MS (m/z, MH+): 427.3.

Quelle