Reaktion #155875

Reaktionsgleichung

diphenylmethanimine

6-bromo-3-ethyl-1-phenyl-1H-indazole

Xantphos

Cs2CO3

→

3-ethyl-1-phenyl-1H-indazol-6-amine

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a 100-mL 3-necked round-bottom flask purged
2. 2
   Temperaturmaintained with an inert atmosphere of nitrogen
3. 3
   TemperaturThe resulting solution was heated
4. 4
   Temperaturto reflux for 16 h in an oil bath
5. 5
   EinengenThe resulting mixture was concentrated under vacuum
6. 6
   workup.DISSOLUTIONThe residue was dissolved in tetrahydrofuran/3N hydrogen chloride (15 mL/5 mL)
7. 7
   Einengenconcentrated under vacuum

Vorschrift

Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 6-bromo-3-ethyl-1-phenyl-1H-indazole (300 mg, 1.00 mmol, 1.00 equiv) in tetrahydrofuran (30 mL), Xantphos (64 mg, 0.11 mmol, 0.11 equiv), Pd(OAc)2 (33 mg, 0.15 mmol, 0.15 equiv), Cs2CO3 (214 mg, 1.11 mmol, 1.11 equiv), diphenylmethanimine (200 mg, 1.10 mmol, 1.10 equiv). The resulting solution was heated to reflux for 16 h in an oil bath. The resulting mixture was concentrated under vacuum. The residue was dissolved in tetrahydrofuran/3N hydrogen chloride (15 mL/5 mL). The resulting solution was stirred for an additional 2 h at room temperature, then concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate:MeOH:NH4OH (30:1:0.3) to yield 3-ethyl-1-phenyl-1H-indazol-6-amine as yellow oil.

Quelle