Cesium carbonate → HCID 86731659, compound

Participants

Reaction Conditions

Reaction Steps

Dioxane (2.7 mL), 2-chloro-N,N,6-trimethylpyridine-4-carboxamide trifluoroacetate (250 mg, 0.80 mmol), and cesium carbonate (782 mg, 2.40 mmol) were added to benzophenone imine (0.134 mL, 0.80 mmol) in a scintillation vial. The vial was purged and flushed with argon 3 times before adding Xantphos (69 mg, 0.12 mmol) and Pd2(dba)3 (73 mg, 0.080 mmol). The vial was purged and flushed with argon 3 times before sealing the system and heating to 80° C. for 10 hours. The reaction mixture was cooled to room temperature, and purified directly by silica gel chromatography (10-80% acetone/hexanes, linear gradient) to afford 2-[(diphenylmethylidene)amino]-N,N,6-trimethylpyridine-4-carboxamide. The isolated material was diluted with DCM (1 mL) and TFA (1 mL). The reaction mixture was stirred at room temperature for 2 hours, and then directly purified by reverse phase HPLC (5-30% acetonitrile/water with 0.1% TFA, linear gradient) to afford 2-amino-N,N,6-trimethylpyridine-4-carboxamide TFA salt. MS ESI calc'd. for C9H14N3O [M+H]+ 180. found 180. 1H NMR (500 MHz, CDCl3) δ 7.09 (s, 1H), 7.03 (s, 1H), 3.06 (s, 3H), 2.91 (s, 3H), 2.52 (s, 3H).

Provenance & Evidence