Reaktion #718080

Reaktionsgleichung

(R,R)-(−)-N,N′-Dimethyl-1,2-cyclohexanediamine

intermediate 113a

4-Iodo-1-[3-(tetrahydro-pyran-2-yloxy)-propyl]-1H-pyrazole

5-tert-butyl-2H-pyrazol-3-ylamine

K2CO3

→

title compound

Ausbeute 73.6%

3-tert-Butyl-1′-[3-(tetrahydro-pyran-2-yloxy)-propyl]-1′H-[1,4′]bipyrazolyl-5-ylamine

Ausbeute 73.6%

Lösungsmittel

water

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepreviously degassed
2. 2
   SonstigeThe crude reaction mixture
3. 3
   Extraktionextracted with EtOAc (×3)
4. 4
   WaschenThe combined organic layers were washed with brine
5. 5
   Trocknendried (MgSO4)
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe resultant residue was purified by FCC on silica

Vorschrift

To a mixture of intermediate 113a (1.50 g, 4.46 mmol), 5-tert-butyl-2H-pyrazol-3-ylamine (620 mg, 4.46 mmol), copper (I) iodide (42 mg, 0.22 mmol) and K2CO3 (1.29 g, 9.37 mmol) was added a solution of toluene (4.6 mL), previously degassed by using a stream of argon. (R,R)-(−)-N,N′-Dimethyl-1,2-cyclohexanediamine (141 μL, 0.89 mmol) was then added and the reaction mixture was heated at 140° C. for 2.5 h under microwave irradiation. The crude reaction mixture was poured into water and extracted with EtOAc (×3). The combined organic layers were washed with brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by FCC on silica, using a gradient of 0-100% EtOAc in cyclohexane, to give the title compound (1.14 g, 73%). LCMS (Method 4): Rt 2.34 min, m/z 348 [MH+].

Quelle