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 (405 mg, 2.6 mmol, 1.1 eq), cesium carbonate (1.54 g, 4.72 mmol, 2 eq), tri-tert-butylphosphinium tetrafluoroborate (137 mg, 0.47 mmol, 0.2 eq), palladium (II) acetate (51 mg, 0.24 mmol, 0.1 eq) and 4-bromo-2-(1-methyl-cyclopropyl)-pyridine (Step 40.4) (500 mg, 2.36 mmol) in DMF (10 mL) is stirred for 3.5 h at 100° C. under an argon atmosphere, allowed to cool, quenched by addition of a saturated solution of NaHCO3 and filtered through a pad of celite. The filtrate is extracted with EtOAc. The organic phase is washed with a saturated solution of NaHCO3, dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (DCM/MeOH, 1:0→99:1) to afford 569 mg of the title compound as a yellow solid: ESI-MS: 288.1 [M+H]+; TLC: Rf=0.40 (DCM/MeOH, 9:1).

Provenance & Evidence