Sodium t-butoxide → HCID 178426486, compound

Participants

Reaction Conditions

Reaction Steps

To a glass microwave reaction vessel was added 2-(3-chloropyrazin-2-yl)-2-methyl-N-(cis-4-((5-methylpyridin-2-yl)amino)cyclohexyl)propanamide (0.1050 g, 0.271 mmol), RuPhos Precatalyst (0.012 g, 0.016 mmol, Strem Chemicals), and sodium tert-butoxide (0.052 g, 0.541 mmol, Sigma-Aldrich Chemical Company, Inc.) in dry dioxane (0.271 ml) to stir at 90° C. for 17 h. Solvent was evaporated in vacuo. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage SNAP HP-silica gel column (25 g), eluting with a gradient of 10% to 100% EtOAc in hexane, to provide the title compound (0.0313 g, 0.089 mmol, 32.9% yield). LCMS showed product peak at 1.526 min (m+1=352.1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.33 (s, 6 H) 1.52 (d, J=11.93 Hz, 2 H) 1.64 (t, J=13.60 Hz, 2 H) 1.98-2.14 (m, 5 H) 2.58 (d, J=10.37 Hz, 2 H) 3.91 (br. s., 1 H) 4.16-4.30 (m, 1 H) 6.16 (br. s., 1 H) 6.58 (d, J=8.41 Hz, 1 H) 7.24 (dd, J=8.31, 2.05 Hz, 1 H) 7.81 (s, 1 H) 8.15 (d, J=3.13 Hz, 1 H) 8.16-8.21 (m, 1 H)

Provenance & Evidence