Reaktion #88937

Reaktionsgleichung

Trans-N,N′-dimethylcyclohexane-1,2-diamine

3-tert butyl-1h-pyrazol-5-amine

Intermediate 62a

3-Bromo-5-chloro-phenol

potassium carbonate

→

title compound

Ausbeute 62.0%

3-(5-Amino-3-tert-butyl-pyrazol-1-yl)-5-chloro-phenol

Ausbeute 62.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas repeatedly purged with argon
2. 2
   Sonstigethe mixture was re-purged with argon
3. 3
   workup.ADDITIONDegassed toluene (4 mL) was added
4. 4
   workup.ADDITIONdiluted with water
5. 5
   Extraktionextracted with EtOAc
6. 6
   SonstigeThe combined organics were dried
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigeThe residue was purified by FCC

Vorschrift

A microwave vial containing 3-tert butyl-1h-pyrazol-5-amine (559 mg, 4.02 mmol), Intermediate 62a (1.00 g, 4.82 mmol), copper(I) iodide (38 mg, 0.20 mmol) and potassium carbonate (1.16 g, 8.44 mmol) was repeatedly purged with argon. Trans-N,N′-dimethylcyclohexane-1,2-diamine (126 μL, 0.80 mmol) was added and the mixture was re-purged with argon. Degassed toluene (4 mL) was added and the resulting suspension was stirred and heated at 110° C. for 24 h. The cooled suspension was passed through Celite pad and diluted with water and extracted with EtOAc. The combined organics were dried and concentrated in vacuo. The residue was purified by FCC, using 0-50% EtOAc in cyclohexane, to give the title compound (620 mg, 62%). LCMS (Method 3): Rt 3.13 min, m/z 266 [MH+].

Quelle