Cesium carbonate → 1,1-dimethylethyl {(2S,3R)-8-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-3-hydroxy-8-azaspiro[4.5]dec-2-yl}carbamate

Participants

Reaction Conditions

Reaction Steps

In a sealed tube, 8-bromo-7-fluoro-2-(methyloxy)-1,5-naphthyridine (500 mg, 1.96 mmol), 1,1-dimethylethyl (3-hydroxy-8-azaspiro[4.5]dec-2-yl)carbamate (530 mg, 1.96 mmol) [prepared according to Example 1], Pd2dba3 (121 mg, 0.117 mmol), rac-Binap (73 mg, 0.117 mmol), Cs2CO3 (1.30 g, 4.11 mmol) and 18-C-6 (52 mg, 0.196 mmol) in dioxane (20 mL) were combined and flushed with N2. After 15 min, the tube was sealed and heated to 100° C. while stirring rapidly. After 12 h, the solution was filtered, concentrated and the residue purified via column chromatography (silica, 1% MeOH in DCM (1% NH4OH)) yielding the title compound (92 mg, 11%) as an orange oil: LCMS (ES) m/e 447 (M+H)+.

Provenance & Evidence