Sodium t-butoxide → HCID 178454102, compound

Participants

Reaction Conditions

Reaction Steps

To a glass microwave reaction vessel was added tert-butyl(cis-3-(2-(3-chloropyrazin-2-yl)-2-methylpropanamido)cyclobutyl)carbamate (0.8210 g, 2.226 mmol), RuPhos Precatalyst (0.097 g, 0.134 mmol, Strem Chemicals), and sodium tert-butoxide (0.428 g, 4.45 mmol, Sigma-Aldrich Chemical Company, Inc.) in dry dioxane (2.226 ml) to stir at 80° C. for 24 h. The 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 (50 g), eluting with a gradient of 40% to 100% EtOAc in hexane, to provide the title compound (0.1812 g, 0.545 mmol, 24.49% yield). LCMS showed product peak at 2.060 min (m+1=333.0). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.31 (s, 3 H) 1.39 (s, 5 H) 2.52-2.58 (m, 1 H) 2.80 (qd, J=9.16, 2.64 Hz, 1 H) 3.68-3.83 (m, 1 H) 4.34-4.47 (m, 1 H) 7.21 (d, J=6.85 Hz, 1 H) 8.13-8.18 (m, 1 H)

Provenance & Evidence