Dichloromethane → N-((1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3'-(methylsulfonyl)biphenyl-4-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 225 mg of 4-bromo-N-((1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)aniline (0.52 mmol), 160 mg of 3-(methylsulfonyl)phenylboronic acid (0.82 mmol), 27 mg of PdCl2(dppf).CH2Cl2 (33 μmol), and 0.5 mL of 3.5 M aqueous K2CO3 (1.75 mmol) in DME (2.5 mL) was placed in a 5 mL microwave reaction vial and heated to 140° C. for 10 minutes in the Biotage Initiator microwave reactor. After cooling to room temperature the vial was opened and the lower aqueous layer was removed by means of a glass pipet. The resulting dark organic solution was diluted with EtOAc, treated with Na2SO4 filtered and concentrated in vacuo to afford a dark oil. The crude product was purified by silica gel flash chromatography on a 12 g column using gradient elution from 0% to 90% EtOAc/hexane. Appropriate fractions were combined and concentrated in vacuo to afford N-((1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3′-(methylsulfonyl)biphenyl-4-amine as a white foam, yield 150 mg (57%): 1H NMR (400 MHz, CDCl3): δ 8.10-8.06 (m, 1H), 7.83-7.77 (m, 2H), 7.61-7.55 (m, 2H), 7.52-7.41 (m, 5H), 7.67 (s, 1H), 6.64-6.59 (m, 2H); MS (ESI) m/z 506.1 [M+H]+.

Provenance & Evidence