Reaktion #90442

Reaktionsgleichung

3,6-Dibromocarbazole

NaN3

L-proline

NaOH

→

desired product

3-azido-6-bromo-9H-carbazole

Lösungsmittel

EtOH H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe completed reaction
2. 2
   Sonstigewas partitioned between EtOAc/H2O (3×)
3. 3
   Waschenthe combined organics were washed with satd
4. 4
   Trocknenaq. NaCl, dried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe crude residue was purified by chromatography (SiO2, 0-15% EtOAc/toluene)

Vorschrift

3,6-Dibromocarbazole (0.500 g, 1.538 mmol), NaN3 (0.120 g, 1.846 mmol), CuI (0.029 g, 0.154 mmol), L-proline (0.053 g, 0.461 mmol) and NaOH (0.019 g, 0.461 mmol) were dissolved in 7:3 EtOH/H2O (3.0 mL) and heated to 95° C. under a N2 atmosphere for 24 h. The completed reaction was partitioned between EtOAc/H2O (3×) and the combined organics were washed with satd. aq. NaCl, dried over Na2SO4, filtered, and concentrated. The crude residue was purified by chromatography (SiO2, 0-15% EtOAc/toluene), followed by HPLC (Phenomenex SiO2 Luna 10 μ, 250×21.2 mm column, 50% EtOAc/Hexane, 21 mL/min, retention time=48 min) to afford the desired product.

Quelle