Cesium carbonate → 5-(3,3-Difluoro-azetidin-1-yl)-6-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid (1-methyl-1-thiazol-2-yl-ethyl)-amide

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-6-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid (1-methyl-1-thiazol-2-yl-ethyl)-amide (Example 288a) (63.6 mg, 150 μmol) in dry toluene (1 ml) was added 3,3-difluoroazetidine hydrochloride (21.4 mg, 165 μmol), BINAP (9.34 mg, 15.0 μmol), Pd(OAc)2 (3.37 mg, 15.0 μmol) and Cs2CO3 (122 mg, 375 μmol). The reaction was stirred at 120° C. overnight and controlled by LC-MS. Evaporation of the volatiles, residue was redissolved in DMF and directly purified by preparative HPLC to give the title compound (21 mg, 48 umol, 32%), MS (EI): m/e=437.4 [M+H]+.

Provenance & Evidence