Morpholine → 3-morpholino-7-(pyridin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-thiazol]-2'-amine

Participants

Reaction Conditions

Reaction Steps

A vial was charged with 3-bromo-7-(pyridin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-thiazol]-2′-amine (0.080 g, 0.117 mmol), palladium diacetate (2.62 mg, 0.012 mmol), sodium tert-butoxide (0.071 ml, 0.583 mmol), and xantphos (0.013 g, 0.023 mmol). Dioxane (1.166 ml) and morpholine (0.030 ml, 0.350 mmol) were added sequentially and the reaction was stirred at 100° C. for 24 hours. The mixture was cooled to RT and was diluted with EtOAc (20 mL) and washed with water. The aqueous layer was extracted with EtOAc (3×15 mL), and the combined organic layers were, dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (RediSep 12 g, gradient elution 0-100% EtOAc:Hex) to afford 3-morpholino-7-(pyridin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-thiazol]-2′-amine as an off-white solid.

Provenance & Evidence