Cesium carbonate → HCID 67980492, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 4-carbamoyl-4-methylpiperidine-1-carboxylate (178 mg, 0.733 mmol), methyl 2-(4-bromobenzyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylate (240 mg, 0.670 mmol), Pd2(dba)3 (61 mg, 0.066 mmol), Xantphos (116 mg, 0.200 mmol), and Cs2CO3 (434 mg, 1.33 mmol) in dioxane (10.6 mL) was degassed thoroughly and the reaction vessel was sealed. The mixture was heated at 100° C. overnight and then filtered. The filtrate was concentrated. The resulting residue was purified by column chromatography (SiO2, 0-90% EtOAc in hexane) to give methyl 2-[4-({[1-(tert-butoxycarbonyl)-4-methylpiperidin-4-yl]carbonyl}amino)benzyl]-1,2,3,4-tetrahydroisoquinoline-6-carboxylate (160 mg, 46%). LC-MS: (FA) ES+ 522; 1H NMR (400 MHz, CDCl3) δ 7.78 (s, 1H), 7.75 (dd, J=8.0, 1.6 Hz, 1H), 7.48 (d, J=8.5 Hz, 2H), 7.33 (dd, J=9.3, 7.0 Hz, 3H), 7.01 (t, J=7.3 Hz, 1H), 3.91-3.83 (m, 3H), 3.67 (dd, J=19.7, 4.9 Hz, 5H), 3.40-3.27 (m, 2H), 3.00-2.85 (m, 2H), 2.73 (t, J=5.9 Hz, 2H), 2.13-1.96 (m, 3H), 1.55 (t, J=21.0 Hz, 2H), 1.46 (d, J=5.0 Hz, 9H), 1.31 (d, J=9.9 Hz, 3H).

Provenance & Evidence