Lithium Hexamethyldisilazide → (5S)-3-(3,3-difluoro-1-pyrrolidinyl)-7-((3-methyl-3-oxetanyl)ethynyl)spiro[chromeno[2,3-c]pyridine-5,4'-[1,3]oxazol]-2'-amine

Participants

Reaction Conditions

Reaction Steps

Tris(dibenzylideneacetone)dipalladium (0) (0.012 g, 0.013 mmol), 2-(dicyclohexylphosphino)-2′-(n,n-dimethylamino)biphenyl (0.015 g, 0.039 mmol), 3,3-difluoropyrolidine HCl, 98% (0.113 g, 0.786 mmol) and (S)-3-chloro-7-((3-methyloxetan-3-yl)ethynyl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine (0.100 g, 0.262 mmol) were combined and degassed with nitrogen. LHMDS (1.06 m solution in THF) (1.571 mL, 1.571 mmol) was added and the mixture was stirred at 90° C. overnight. The solvent was removed and the crude material was purified by column chromatography with 0-5% 2M NH3 in MeOH/CH2Cl2 to provide the desired product as an off white solid. MS m/z=452.9 [M+H].

Provenance & Evidence