Methyl 3-mercaptopropionate → HCID 86761411, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with tris(dibenzylideneacetone)dipalladium (0) (0.05539 g, 0.06049 mmol), 5-bromo-N-(4-methylthiazol-2-yl)-4-(quinolin-5-yloxy)pyridin-2-amine (0.500 g, 1.210 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.05250 g, 0.09074 mmol), methyl 3-mercaptopropanoate (0.5360 ml, 4.839 mmol), and N-ethyl-N-isopropylpropan-2-anine (0.4215 ml, 2.420 mmol), and degassed dioxane (40 mL) was added. The reaction was stirred at 93° C. overnight. Water was added and the reaction was extracted with ethyl acetate. The organic layer was dried, filtered and concentrated. The residue was purified using silica gel column chromatography with 20-30-40-60-80% ethyl acetate in hexanes and then with ethyl acetate to give the desired product (0.469 g, 85% yield) as yellow solid. 1H NMR (CDCl3) δ 8.93 (m, 1H), 8.37 (d, 1H), 8.19 (m, 1H), 8.02 (dd, 1H), 7.66 (t, 1H), 7.36 (dd, 1H), 7.19 (d, 2H), 6.11 (s, 1H), 3.60 (s, 3H), 2.60 (t, 2H), 1.71 (s, 3H), 1.22 (t, 2H).

Provenance & Evidence