Cesium carbonate → N-{4-methyl-5-[2-(1-methyl-cyclopropyl)-pyridin-4-yl]-thiazol-2-yl}-acetamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-acetamido-4-methylthiazole [7336-51-8] (60.4 mmol), cesium carbonate (110 mmol), tri-tert-butylphosphinium tetrafluoroborate (10.99 mmol), palladium (II) acetate (5.49 mmol) and 4-bromo-2-(1-methyl-cyclopropyl)-pyridine (Step 1.4) (54.9 mmol) in DMF (230 mL) was stirred for 3.5 h at 100° C. After cooling to rt, the reaction mixture was filtered and then concentrated. The residue was diluted with a saturated solution of NaHCO3 and extracted with EtOAc (3×). The combined organic phases were successively washed with a saturated solution of NaHCO3 and brine, dried (Na2SO4), filtered and concentrated. The residue was purified using a RediSep® silica gel column to afford the title compound as a pale yellow solid. HPLC: tR=4.37 min (method B); LC-MS: tR=1.47 min, [M+H]+ 288; TLC: Rf=0.26 (1:2 Hex/EtOAc).

Provenance & Evidence