3-METHYL-4-BROMOACETANILIDE → HCID 58094433, compound

Participants

Reaction Conditions

Reaction Steps

Under N2 atmosphere, to a mixture of (R)-2-methylmorpholine HCl salt (1.1 g, 8 mmol), N-(4-bromo-3-methylphenyl)acetamide (1.7 g, 7.45 mmol), Pd2 dba3 (92 mg, 0.1 mmol) and 2-(di-t-butylphosphino)biphenyl (72 mg, 0.24 mmol) was added LiHMDS (28 mmol, 28 mL, 1 M in THF). The resulting mixture was stirred at 65° C. overnight. THF was removed under reduced pressure. The residue was treated with HCl (1N), basified with NaHCO3, and then extracted with EtOAc. The combined organics was washed with brine and dried over Na2SO4. The crude was purified by flash chromatography on silica gel (40-100% EtOAc in hexanes) to afford the product as a yellow solid.

Provenance & Evidence