Sodium Carbonate → N-[5-(2,4-difluorophenyl)-3-(2-methoxyethyl)-1,3-thiazol-2(3H)-ylidene]acetamide

Participants

Reaction Conditions

Reaction Steps

A flask was charged with the product from Example 197A (10.2 g, 42.6 mmol), 2,6-difluorophenylboronic acid (8.08 g, 51.1 mmol), Na2CO3 (64.0 mL of a 2 M aqueous solution, 128 mmol) and PdCl2(PPh3)2 (1.5 g, 2.13 mmol) in 100 mL of DME/H2O/ethanol (7:3:2). The mixture was warmed to 85° C. and stirred overnight. After cooling to room temperature, the mixture was diluted with ethyl acetate and washed with water. The organic extract was dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography on SiO2 using a gradient of 0% to 100% ethyl acetate: hexane to provide 11.5 g (86%) of the title compound: 1H NMR (300 MHz, CDCl3) δ 2.17 (s, 3H) 3.27 (s, 3H) 3.71 (t, J=5.3 Hz, 2H) 4.37 (t, J=5.4 Hz, 2H) 7.17-7.24 (m, 1H) 7.38-7.48 (m, 1H) 7.64-7.74 (m, 1H) 7.88 (s, 1H); MS (ESI+) m/z 313 (M+H)+.

Provenance & Evidence