Cesium carbonate → 2-Fluoro-3-methyl-6-(2H-1,2,3-triazol-2-yl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

The title compound was prepared in analogy to the procedure described in WO2008/069997. Cs2CO3 (6.98 g, 21.4 mmol) was added portionwise to a RT solution of 2-fluoro-6-iodo-3-methyl-benzoic acid (3.0 g, 10.7 mmol) in DMF (15 mL) under argon followed by 1H-1,2,3-triazole (1.24 mL, 21.4 mmol) and Cu(I)I (103 mg, 0.536 mmol) and the resulting blue suspension was stirred at 80° C. overnight. The reaction mixture was quenched with 2M aq. HCl and filtered through a celite plug before being extracted with DCM (3×). The combined organic layers were dried over Na2SO4, filtered and evaporated in vacuo to give the crude product that was purified by prep. HPLC (method E) to give the title compound as a pale yellow solid. LC-MS B: tR=0.55 min; [M+H]+=222.01.

Provenance & Evidence