Reaktion #88908

Reaktionsgleichung

3-(Tert-butyl)-1H-pyrazol-5-amine

potassium carbonate

3-Bromo-5-chloro-benzoic acid ethyl ester

→

title compound

Ausbeute 19.2%

3-(5-Amino-3-tert-butyl-pyrazol-1-yl)-5-chloro-benzoic acid ethyl ester

Ausbeute 19.2%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepurged with argon
2. 2
   Sonstigethe reaction vessel purged with argon
3. 3
   Sonstigedegassed with argon
4. 4
   Sonstigesealed
5. 5
   Sonstigesubjected to microwave irradiation (135° C., 6 h)
6. 6
   FiltrationThe reaction mixture was filtered through Celite
7. 7
   Einengenconcentrated in vacuo
8. 8
   Sonstigepurified by FCC
9. 9
   Wascheneluting with 0-10% EtOAc/cyclohexane

Vorschrift

3-(Tert-butyl)-1H-pyrazol-5-amine (1.10 g, 7.90 mmol), potassium carbonate (2.29 g, 16.6 mmol), and copper (I) iodide (75.0 mg, 1.58 mmol) were weighed into a microwave vial and purged with argon. 3-Bromo-5-chloro-benzoic acid ethyl ester (2.50 g, 9.49 mmol) was then added, followed by trans-N,N′-dimethylcyclohexane-diamine (225 mg, 1.58 mmol) and the reaction vessel purged with argon. The reagents were then solvated with toluene (8 mL), and then degassed with argon, sealed and subjected to microwave irradiation (135° C., 6 h). The reaction mixture was filtered through Celite, concentrated in vacuo and purified by FCC, eluting with 0-10% EtOAc/cyclohexane, to afford the title compound (489 mg, 19%). LCMS (Method 3) Rt 4.26 min, 322.1 [MH+].

Quelle