Réaction #1563867

Équation de réaction

K2CO3

4-Bromo-1-phenyl-1H-pyrazole

thiophen-2-ylboronic acid

→

1-phenyl-4-(thiophen-2-yl)-1H-pyrazole

Rendement 27.6%

Solvants

toluene-methanol

Conditions de réaction

Traitement

1. 1
   FiltrationThe reaction mixture was then filtered
2. 2
   Lavagewashed with toluene-methanol (5 ml)
3. 3
   Concentrationthe filtrate was concentrated
4. 4
   Autrecolumn purified

Mode opératoire

4-Bromo-1-phenyl-1H-pyrazole (150 mg, 0.672 mmol), thiophen-2-ylboronic acid (296 mg, 2.31 mmol), PEPPSI-iPr (13.6 mg, 0.062 mmol), and K2CO3 (480 mg, 3.48 mmol) were combined in toluene-methanol (1:1) (2 ml). The reaction mixture was heated under microwave at 80° C. for 10 minutes. The reaction mixture was then filtered and washed with toluene-methanol (5 ml), and the filtrate was concentrated. The crude mixture was then column purified using 15-20% ethyl acetate/hexane to yield 1-phenyl-4-(thiophen-2-yl)-1H-pyrazole (42 mg, yield 27%). The HPLC purity of the final product was 99.32%. LC-MS [M+H] 227 (C13H10N2S+H expected 227.06). The 1H-NMR spectra was in accordance with the chemical structure.

Source