Sodium Bicarbonate → HCID 136501884, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-(4-bromo-phenyl)-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (58.0 mg, 0.200 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (45.8 mg, 0.22 mmol) and sodium hydrogen carbonate (20.2 mg, 0.24 mmol) in 0.4 ml DMF and 0.2 ml water is flushed with nitrogen and heated to 40° C. Then bis(triphenylphosphine)-palladium(II)-chloride (2.8 mg, 0.004 mmol) is added. The reaction mixture is heated to 80° C. and stirred at this temperature for 18 hours. The mixture is allowed to cool to room temperature and excess water is added. The resulting precipitate is filtered off washed with water and dried under vacuum. The residue is chromatographed on a silica gel column with methanol/dichloromethane as eluent to afford 2-[4-(1-ethyl-1H-pyrazol-4-yl)-phenyl]-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one as off-white crystals; HPLC/MS 1.64 min (C), [M+H] 292;

Provenance & Evidence