2-Amino-3-methylpyridine → HCID 178426305, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S,Z)—N-(7-bromo-3-chloro-1-fluorospiro[chromeno[2,3-c]pyridine-5,4′-[1,3]oxazinan]-2′-ylidene)benzamide (0.25 g, 0.497 mmol), 2-amino-3-picoline (0.055 ml, 0.547 mmol), pd2(dba)3 (0.023 g, 0.025 mmol) and 2-di-t-butylphosphino-2,4,6-tri-1-propyl-1,1-biphenyl (0.037 g, 0.087 mmol) was purged with N2 followed by the addition of toluene (2 mL) and lithium bis(trimethylsilyl)amide (1.243 ml, 1.243 mmol). The resulting mixture was heated at 100° C. and after 30 min the reaction was cooled, diluted with EtOAc and washed with saturated NH4Cl. The organic phase was dried over Na2SO4, filtered, concentrated and chromatographed on silica gel using 0-100% EtOAc/hexanes. The product was repurified by HPLC to afford (S,Z)—N-(3-chloro-1-fluoro-7-((3-methylpyridin-2-yl)amino)spiro[chromeno[2,3-c]pyridine-5,4′-[1,3]oxazinan]-2′-ylidene)benzamide (0.069 g, 0.130 mmol, 26% yield).

Provenance & Evidence