Triphenylphosphine → 1-(4-(5-(5-bromo-3-(6,7-dihydro-5H-cyclopenta[b]pyridin-5-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-yl)ethanone

Participants

Reaction Steps

1-(4-(5-(5-Bromo-3-hydroxypyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-yl)ethanone (0.083 g, 0.21 mmol), 6,7-dihydro-5H-cyclopenta[b]pyridin-5-ol (0.028 g, 0.21 mmol) and triphenylphosphine (0.057 g, 0.22 mmol) were combined in THF (1 mL) under nitrogen. Diisopropyl azodicarboxylate (0.043 ml, 0.22 mmol) was added in one portion. The reaction stirred at ambient temperature overnight. The solution was diluted with water, extracted with CH2Cl2, dried (Na2SO4), filtered and concentrated. Flash chromatography gave 1-(4-(5-(5-bromo-3-(6,7-dihydro-5H-cyclopenta[b]pyridin-5-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-yl)ethanone (0.022 g, 21%); Mass spectrum (apci) m/z=515.0, 517.0 (M+H).

Provenance & Evidence