Lithium Hexamethyldisilazide → HCID 78162559, compound

Participants

Reaction Steps

To a stirred solution of methyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)-5-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate (326b) (0.13 g, 0.27 mmol) in p-dioxane (2 mL) was added LiHMDS (1.64 mL, 1.64 mmol) dropwise. After the addition, the mixture was stirred at RT in overnight, then heated at 60° C. in 1 h, cooled to RT, and quenched with saturated aq. NH4Cl, extracted with EtOAc (3×). The extracts were dried over MgSO4, filtered, concentrated and purified by ISCO (0-70% EtOAc/Hexanes) to give the title compound (43 mg, 35%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.09 (1H, s), 7.78 (1H, dd, J=7.4, 1.4 Hz), 7.67 (1H, dd, J=8.2, 1.4 Hz), 7.38 (1H, t, J=7.7 Hz), 6.94 (1H, s), 6.00 (1H, s), 4.99 (1H, q, J=6.5 Hz), 2.56 (3H, s), 1.59 (3H, d, J=6.5 Hz), 1.52 (9H, s), 1.51 (9H, s). m/z (ESI, +ve) 450.0 (M+H)+.

Provenance & Evidence