Water → HCID 45137948, compound

Participants

Reaction Steps

To a mixture of (R)-3-bromo-5-(2-(hydroxymethyl)pyrrolidin-1-yl)-N-((6-methylpyridin-3-yl)methyl)benzamide (45 mg, 0.11 mmol), p-tolylboronic acid (16 mg, 0.12 mmol), Toluene (3 mL, 30 mmol), cesium carbonate (4.0E1 mg, 0.12 mmol), and Water (0.2 mL, 8 mmol) under argon was added Tetrakis(triphenylphosphine)palladium(0) (6.4 mg, 0.0055 mmol). The mixture was heated under reflux for 5 h. After cooling, the mixture was filtered through Celite and the filter cake was washed with EtOAc. The filtrate was washed with brine, dried (Na2SO4), and concentrated. The residue was purified by preparative HPLC (100×21.2 mm C18 column, 30-80% CH3CN/water [10 mM Et2NH]) to afford a white foam. LC-MS: 2.09 min, 416.5 [M+1]+; HPLC: 9.12 min.

Provenance & Evidence