Réaction #41131

Équation de réaction

1-tert-butyl-5-chloro-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

pyrazole

KF

→

2′-tert-butyl-2′H-[1,3′]bipyrazolyl-4′-carboxylic acid adamantan-2-ylamide

Rendement 41.0%

Solvants

DMSO

Conditions de réaction

Traitement

1. 1
   AutreThe tube was sealed with a septum
2. 2
   Autrewas submitted to 150 W microwave irradiation
3. 3
   Autrea Personal Chemistry Microwave Synthesis system (Biotage AB, Sweden) at 230° C. for 20 minutes
4. 4
   AutreThe reaction mixture was partitioned between ethyl acetate and water
5. 5
   Extractionthe aqueous phase was extracted three times with ethyl acetate
6. 6
   Concentrationconcentrated in vacuo
7. 7
   Autrepurified by C-18

Mode opératoire

In a Personal Chemistry microwave process tube (Biotage AB, Sweden), 1-tert-butyl-5-chloro-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (Example 36, 100 mg, 0.30 mmol), pyrazole (41 mg, 0.60 mmol), KF (35 mg, 0.60 mmol) and DMSO (2 mL) were well mixed. The tube was sealed with a septum and was submitted to 150 W microwave irradiation using a Personal Chemistry Microwave Synthesis system (Biotage AB, Sweden) at 230° C. for 20 minutes. The reaction mixture was partitioned between ethyl acetate and water and the aqueous phase was extracted three times with ethyl acetate. The organic phases were combined, concentrated in vacuo and purified by C-18 reversed phase prep-HPLC with a gradient of 10-100% acetonitrile/water to give 2′-tert-butyl-2′H-[1,3′]bipyrazolyl-4′-carboxylic acid adamantan-2-ylamide (45 mg, 41%). Mass spectrum: m/z: 368.2 (M+1).

Source