Water → HCID 57898991, compound

Participants

Reaction Conditions

Reaction Steps

Degassed toluene (10 mL) was added to a mixture of 2-chloro-3-fluoro-4-(phenylthio)pyridine (0.500 g, 2.09 mmol), 4-methylthiazol-2-amine (0.238 g, 2.09 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.0955 g, 0.104 mmol) and potassium phosphate (0.487 g, 2.29 mmol), and then degassed water (3 mL) was added. The reaction was stirred overnight at 90° C., then partitioned between ethyl acetate and water, washed with brine, dried, and concentrated. The crude material was purified by MPLC (Biotage), eluting with 3:1 hexane:ethyl acetate to afford the desired product (0.364 g, 55.0% yield) as white crystals. 1H NMR (d6-DMSO) δ 2.24 (s, 3H), 6.21 (t, 1H), 6.56 (s, 1H), 7.52-7.61 (m, 5H), 7.93 (d, 1H), 11.35 (bs, 1H).

Provenance & Evidence