Reaktion #1948310

Reaktionsgleichung

water

3-formyl-1H-indazole-6-carboxylic acid

1,2-phenylenediamine

sulfur

→

3-(1H-benzoimidazol-2-yl)-1H-indazole-6-carboxylic acid

Ausbeute 90.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThis mixture was then heated
2. 2
   Temperaturto reflux for 6 hours
3. 3
   TemperaturAfter cooling
4. 4
   Sonstigethe brown precipitate which formed
5. 5
   Filtrationwas filtered
6. 6
   Sonstigecollected

Vorschrift

To 3-formyl-1H-indazole-6-carboxylic acid (2.35 g, 12.42 mmol) in DMF (60mL) was added 1,2-phenylenediamine (12.42 mmol, 1.34 g) and sulfur powder (1.1 eq, 13.66 mmol). This mixture was then heated to reflux for 6 hours. The reaction was followed by TLC and LC-MS. After cooling, water (50 mL) was added to the reaction and the brown precipitate which formed was filtered and collected to provide 3.1 g (90%) of 3-(1H-benzoimidazol-2-yl)-1H-indazole-6-carboxylic acid. 1H NMR (DMSO-d6) δ 14.01 (1H, s), 8.58 (1H, d, J=8.5 Hz), 8.24 (1H, s), 7.87 (1H, d, J=8.7 Hz), 7.64 (2H, m), 7.25 (2H, m). MS (APCI positive) 279.

Quelle