Réaction #88959

Équation de réaction

diethylazodicarboxylate

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

Ph3P

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

→

title compound

Rendement 96.0%

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

Rendement 96.0%

Solvants

THF

Conditions de réaction

Traitement

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

Mode opératoire

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+].

Source