Reaktion #88959

Reaktionsgleichung

diethylazodicarboxylate

5-(5-amino-3-tert-butyl-pyrazol-1-yl)-2-chloro-phenol

Ph3P

3-(tetrahydro-pyran-2-yloxy)-propan-1-ol

→

title compound

Ausbeute 96.0%

5-tert-Butyl-2-{4-chloro-3-[3-(tetrahydro-pyran-2-yloxy)-propoxy]-phenyl}-2H-pyrazol-3-ylamine

Ausbeute 96.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm up to RT
2. 2
   SonstigeThe volatiles were removed under reduced pressure
3. 3
   SonstigeThe residue was purified by FCC

Vorschrift

To a solution of 5-(5-amino-3-tert-butyl-pyrazol-1-yl)-2-chloro-phenol (WO2011/154734A1, which is incorporated herein by reference in it is entirety; 500 mg, 1.88 mmol), and Ph3P (986 mg, 3.76 mmol) in dry THF (10 mL) was added 3-(tetrahydro-pyran-2-yloxy)-propan-1-ol (Can. J. Chem. Vol. 73, 1195, pp 1682, which is incorporated herein by reference in it is entirety; 452 mg, 2.82 mmol). The resulting mixture was cooled to 0° C. using an ice bath and diethylazodicarboxylate (0.69 mL, 3.76 mmol) was added to the chilled mixture which was allowed to warm up to RT. The volatiles were removed under reduced pressure. The residue was purified by FCC, using 0-50% EtOAc in cyclohexane, to give the title compound (739 mg, 96%). LCMS (Method 1): Rt 3.63 min, m/z 408 [MH+].

Quelle