Cesium carbonate → HCID 59302498, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 2-(4-(3-fluoro-4-(trifluoromethylsulfonyloxy)phenyl)cyclohexyl)acetate (190 mg, 0.477 mmol), 2-{[tert-butyl(dimethyl)silyl]oxy}ethanamine (100 mg, 0.572 mmol), cesium carbonate (171 mg, 0.525 mmol), palladium acetate (11 mg, 0.048 mmol) and (X-PHOS) (23 mg, 0.048 mmol) in toluene (5 mL), under nitrogen, was heated in a sealed tube at 120° C. for 16 hours. The reaction was cooled, diluted into EtOAc, washed with water (2×), saturated aqueous brine, dried over sodium sulfate and concentrated to afford a dark oil. Chromatography (12 g silica gel column, 3-15% EtOAc:heptane) afforded methyl 2-(4-(4-(2-(tert-butyldimethyl-silyloxy)ethylamino)-3-fluorophenyl)-cyclohexyl)acetate as a light-yellow oil, 110 mg. 1H NMR (400 MHz, CDCl3); δ 7.2 (m, 1H), 6.95 (m, 1H), 6.8 (m, 1H), 3.8 (m, 2H), 3.64 (s, 3H), 3.2 (m, 2H), 2.5, 2.3 (m, 1H), 2.4, 2.2 (d, 2H), 1.85 (m, 2H), 1.64 (m, 5H), 1.4 (m, 1H), 1.1 (m, 1H), 0.88 (s, 9H), 0.06 (s, 6H). m/z=424.2 (M+1).

Provenance & Evidence