Phosphoric Acid → HCID 131734952, compound

Participants

Reaction Conditions

Reaction Steps

A vial was charged with 1,3,5-trimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.117 g, 0.498 mmol), tert-butyl (3-bromo-2-chloro-5-cyanophenyl)carbamate (0.15 g, 0.452 mmol), PdCl2(DPPF) (0.033 g, 0.045 mmol) and dioxane (3.62 ml). The slurry was evacuated and backfilled with nitrogen (4×). Phosphoric acid, potassium salt (0.588 ml, 1.176 mmol) was added and the vial was capped and warmed to 85° C. 2 h. The reaction mixture was diluted with ethyl acetate and vacuum filtered through a pad of Celite. The filtrate was concentrated and the crude residue purified by column chromatography on the ISCO system (12 g, 0-70% EtOAc/Hex) to provide tert-butyl (2-chloro-5-cyano-3-(1,3,5-trimethyl-1H-pyrazol-4-yl)phenyl)carbamate (82.7 mg) as a yellow oil.

Provenance & Evidence