Tetrahydrofuran → HCID 86627643, compound

Participants

Reaction Steps

(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[3-(5-chloro-2-fluorophenyl)pyrazin-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one (33 mg, 0.062 mmol), methyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (INTERMEDIATE 37, 14.39 mg, 0.052 mmol), 1,1′-bis(di-tert-butylphosphino) ferrocene palladium dichloride (6.30 mg, 9.27 mmol), K2CO3 (0.155 mL, 0.309 mmol) and THF (1 mL) were sealed in a microwave vessel and subjected to microwave irradiation at 140° C. for 20 min. LCMS of aliquot indicated about 40% conversion. Microwave heating was resumed at 140° C. for an additional 30 min. LCMS of the aliquot indicated about 10% of remaining unreacted starting material. Microwave heating was resumed for an additional 12 min at 140° C. The resulting crude material was diluted with MeCN and filtered. The filtrate was purified by preparative HPLC (Kromasil 100-5C18, 100×21.1 mm) eluting with MeCN/water+0.1% TFA (10% to 100% organic in 10 min, hold 100% in 2 min, 20 mL/min) to give a brown glass. The brown glass was further purified by preparative TLC (SiO2, 30% EtOAc/hexanes) to afford a colorless glass as the titled compound. LCMS calc.=647.17; found=648.38 (M+H)+.

Provenance & Evidence