Potassium Carbonate → HCID 70976575, compound

Participants

Reaction Conditions

Reaction Steps

To a flask charged with tert-butyl ((2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)carbamate (for a preparation see Intermediate 29)(5 g, 13.05 mmol), (4-(methoxycarbonyl)phenyl)boronic acid (2.58 g, 14.35 mmol), tetrakis(triphenylphosphine)palladium (0) (1.507 g, 1.305 mmol) and potassium carbonate (5.41 g, 39.1 mmol) was added DME (50 mL) and water (10.0 mL) and the resulting mixture was stirred at 100° C. under nitrogen for 1 h. The reaction was cooled to room temperature and most of the DME was evaporated in vacuo. The residue was partitioned between EtOAc and water and the layers were separated. The aqueous phase was extracted with EtOAc and the combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo. the residue was purified by chromatography, eluting with an EtOAc/hexanes gradient; which gave methyl 4-((2S,4R)-1-acetyl-4-((tert-butoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (5.35 g, 12.20 mmol, 94% yield) as a white foam. LCMS (HpH, 2 min), Rt=1.18 min, MH+=439.

Provenance & Evidence