Reaktion #1137821

Reaktionsgleichung

3-(1H-indazol-1-yl)phenol

2-bromo-9-(pyridin-2-yl)-9H-carbazole

picolinic acid

K3PO4

→

desired product

Ausbeute 88.0%

2-(3-(1H-indazol-1-yl)phenoxy)-9-(pyridin-2-yl)-9H-carbazole

Ausbeute 88.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a dry Shlenck tube equipped with a magnetic stir bar
2. 2
   SonstigeThe tube was evacuated
3. 3
   workup.ADDITIONThen solvent DMSO (9 mL) was added under the protection of nitrogen
4. 4
   Temperaturcooled down to ambient temperature
5. 5
   workup.ADDITIONWater was added
6. 6
   workup.DISSOLUTIONto dissolve the solid
7. 7
   ExtraktionThe mixture was extracted with ethyl acetate three times
8. 8
   WaschenThe combined organic layer was washed with water three time
9. 9
   Trocknendried over sodium sulfate
10. 10
    Filtrationfiltered
11. 11
    SonstigeThe solvent was removed under reduced pressure
12. 12
    Sonstigethe residue was purified through column chromatography on silica gel

Vorschrift

To a dry Shlenck tube equipped with a magnetic stir bar was added 3-(1H-indazol-1-yl)phenol 2 (630 mg, 3.0 mmol, 1.0 eq), 2-bromo-9-(pyridin-2-yl)-9H-carbazole (1163 mg, 3.6 mmol, 1.2 eq), CuI (57 mg, 0.3 mmol, 0.1 eq), picolinic acid (74 mg, 0.6 mmol, 0.2 eq) and K3PO4 (1273 mg, 6.0 mmol, 2.0 eq). The tube was evacuated and backfilled with nitrogen. The evacuation and backfill procedure was repeated for another twice. Then solvent DMSO (9 mL) was added under the protection of nitrogen. The mixture was stirred in an oil bath at a temperature of 90-100° C. for 3 days and then cooled down to ambient temperature. Water was added to dissolve the solid. The mixture was extracted with ethyl acetate three times. The combined organic layer was washed with water three time, dried over sodium sulfate, and then filtered. The solvent was removed under reduced pressure, and the residue was purified through column chromatography on silica gel using hexane/ethyl acetate (10:1-5:1-3:1) as eluent to obtain the desired product Ligand ON12 as a colorless solid 1200 mg in 88% yield. 1H NMR (DMSO-d6, 400 MHz): δ 7.05-7.08 (m, 1H), 7.15 (dd, J=8.4, 2.0 Hz, 1H), 7.24 (t, J=8.0 Hz, 1H), 7.32-7.36 (m, 2H), 7.42-7.47 (m, 3H), 7.52-7.59 (m, 2H), 7.61 (d, J=2.0 Hz, 1H), 7.77-7.83 (m, 3H), 7.86 (d, J=8.0 Hz, 1H), 8.07 (td, J=7.6, 2.0 Hz, 1H), 8.23 (d, J=7.6 Hz, 1H), 8.29 (d, J=7.6 Hz, 1H), 8.33 (s, 1H), 8.66 (dd, J=5.2, 1.6 Hz, 1H). 13C NMR (DMSO-d6, 100 MHz): δ 102.73, 110.40, 111.12, 113.54, 115.66, 116.09, 119.05, 120.28, 120.22, 121.26, 121.56, 121.82, 122.12, 123.24, 125.16, 126.02, 127.64, 131.09, 136.02, 138.01, 139.35, 139.53, 139.94, 140.98, 149.52, 150.45, 154.58, 158.62.

Quelle