Pyridine → HCID 59261368, compound

Participants

Reaction Steps

To a 50 mL round-bottomed flask was added 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (2.0 g, 7.6 mmol) and thionyl chloride (14 ml, 191 mmol) and the reaction mixture was stirred at RT for 1 h. Excess thionyl chloride was evaporated under vacuum and the remaining trace amount was removed azeotropically by addition of toluene (5 mL) and repeated concentration under reduced pressure. To the resulting residue was added DCM (10 mL) followed by 1-methyl-1H-pyrazol-5-amine (1.1 g, 11 mmol) and pyridine (1.2 ml, 15 mmol). The reaction was stirred at reflux for 1 h then cooled to RT. The mixture was diluted with DCM, washed with water followed by sat. NaHCO3, dried over MgSO4, filtered and concentrated in vacuo. The brown residue was loaded on an ISCO 40 g column (eluted with 25-65% EtOAc in Hexanes) and purified to provide the title compound as an off-white amorphous solid. MS (ESI, pos. ion) m/z: 342.2 (M+1).

Provenance & Evidence