Morpholine → HCID 68621414, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-[(6-chloropyridin-3-yl)methyl]-2-[(1S,2S)-2-hydroxycyclohexyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one (0.101 g, 0.248 mmol) in 3 mL of toluene was added morpholine (0.032 g, 0.37 mmol), sodium tert-butoxide (0.60 g, 0.62 mmol), tris[dibenzylideneacetone]dipalladium (0) (0.034 g, 0.037 mmol), and (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.011 g, 0.017 mmol). The mixture was heated at 110° C. for 3 hr, cooled to ambient temperature, poured into saturated aqueous sodium bicarbonate (25 mL), and extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via preparative reverse phase HPLC to provide the title compound that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 458.2 for [M+H]+: 1H NMR (400 MHz, CDCl3) δ 8.15 (s, 1H), 8.10-8.07 (m, 1H), 7.88-7.86 (m, 1H), 7.68 (s, 1H), 7.59-7.56 (m, 2H), 7.28-7.25 (m, 1H), 6.53 (d, J=8.8 Hz, 1H), 4.82-4.69 (m, 2H), 4.33 (s, 2H), 4.20-4.11 (m, 1H), 3.82-3.70 (m, 5H), 3.46-3.41 (m, 4H), 2.23-2.20 (m, 1H), 2.05-1.98 (m, 1H), 1.87-1.64 (m, 4H), 1.51-1.28 (m, 3H) ppm.

Provenance & Evidence