Morpholine → HCID 57421817, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-chloro-3-hydroxypyridine (0.2 g, 1.6 mmol), morpholine (0.7 mL, 8.0 mmol), 2-(dicyclohexylphosphino)-2′,4′,6′,-triisopropyl-biphenyl, (X-Phos) (0.12 g, 0.26 mmol), and tris(dibenzylideneacetone)dipalladium (0) (0.06 g, 0.07 mmol) in dry THF (2.0 mL) was degassed by nitrogen. To this mixture was added 1.0M lithium bis(trimethylsilyl)amide in THF (8.8 mL, 8.8 mmol) dropwise, and the resulting reaction was heated to 60° C. After 20.5 h, the reaction was cooled to rt then concd. The residue was purified on silica gel (0-100% of a premixed solution of 89:9:1 DCM:methanol:ammonium hydroxide in DCM) to afford an off white solid as 5-morpholinopyridin-3-ol. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.62 (1H, br. s.), 7.79 (1H, d, J=2.4 Hz), 7.61 (1H, d, J=2.2 Hz), 6.65 (1H, t, J=2.4 Hz), 3.79 (4H, m), 3.16 (4H, m). Mass Spectrum (pos.) m/e: 181.0 (M+H)+.

Provenance & Evidence