Dichloromethane → HCID 54761628, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 57.0 mg (0.300 mmol) of (3-trifluoromethylphenyl)boronic acid and 76.7 mg (0.200 mmol) of N2-tert-butyl-7-bromo-6-cyclopropyl-3,4-dihydropyrrolo-[1,2-a]pyrazine-2,8(1H)-dicarboxamide in a reaction tube are added 2 ml of tetrahydrofuran degassed beforehand under argon for 15 minutes and 63.6 mg (0.60 mmol) of disodium carbonate dissolved in 1 ml of water. The tube is then purged with argon, and about 16 mg (0.02 mmol) of a complex of 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium (II) and dichloromethane (PdCl2(dppf).CH2Cl2—CAS 95464-05-4) suspended in 2 ml of tetrahydrofuran degassed beforehand under argon are added. The tube is then stirred at 70° C. for 20 hours, the mixture is cooled and the solvent is evaporated off under reduced pressure. The residue is taken up in 5 ml of tetrahydrofuran and 100 mg of propanethiol-grafted silica (Si-Thiol, Biotage) are added. The mixture is stirred for 4 hours at room temperature and the grafted silica is separated out by filtration on a Celite cartridge, the Celite is washed twice with 1 ml of tetrahydrofuran and the filtrate is concentrated under reduced pressure. The residue is then purified by SFC purification, to give 0.017 g of N2-tert-butyl-6-cyclopropyl-7-(3-trifluoromethyl-phenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxamide.

Provenance & Evidence