Lithium Hexamethyldisilazide → HCID 178507231, compound

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with (S,Z)—N-(7-bromo-3-chloro-1-fluorospiro[chromeno[2,3-c]pyridine-5,4′-[1,3]oxazinan]-2′-ylidene)benzamide (2.0 g, 3.98 mmol), Pd(dba)2 (0.073 g, 0.080 mmol) and (2-biphenyl)dicyclohexylphosphine (0.067 g, 0.191 mmol), sealed and purged with N2 followed by the addition of THF (2 mL) and lithium bis(trimethylsilyl)amide, 1.0 m solution in tetrahydrofuran (8.75 ml, 8.75 mmol). The resulting mixture was heated at 65° C. for 17 h, quenched with saturated NH4Cl. The mixture was diluted with EtOAc, washed with water, brine, and dried over Na2SO4. The solution was concentrated and chromatographed on silica gel using 0-100% EtOAc/hexanes to afford a yellow oil as (S,Z)—N-(7-amino-3-chloro-1-fluorospiro[chromeno[2,3-c]pyridine-5,4′-[1,3]oxazinan]-2′-ylidene)benzamide.

Provenance & Evidence