2,6-Dimethylthiophenol → 1-(4-(5-(5-(2,6-Dimethylphenylthio)-3-(2-methylpyridin-3-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-yl)ethanone

Participants

Reaction Conditions

Reaction Steps

1-(4-(5-(5-bromo-3-(2-methylpyridin-3-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-yl)ethanone (0.10 g, 0.20 mmol), xantphos (0.059 g, 0.10 mmol), K3PO4 (0.11 g, 0.53 mmol), and Pd2dba3 (0.047 g, 0.051 mmol) were diluted in degassed toluene (2 mL). 2,6-dimethylbenzenethiol (0.041 mL, 0.31 mmol) was added and the reaction stirred at 110° C. overnight. The solution was cooled and flash chromatographed (10% MeOH/EtOAc) to give 1-(4-(5-(5-(2,6-dimethylphenylthio)-3-(2-methylpyridin-3-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-yl)ethanone (0.051 g, 46% yield) as a tan solid. 1H NMR (CDCl3) δ 1.77-1.94 (m, 4H), 2.10 (s, 3H), 2.38 (s, 6H), 2.43 (s, 3H), 2.80 (t, 1H), 3.04 (t, 1H), 3.20 (t, 1H), 3.88 (s, 1H), 4.53 (d, 1H), 6.53 (s, 1H), 7.13-7.23 (m, 5H), 7.64 (s, 1H), 8.42 (s, 1H), 9.02 (bs, 1H).

Provenance & Evidence