1,2-Dimethoxyethane → HCID 70976485, compound

Participants

Reaction Conditions

Reaction Steps

To a flask charged with (2S,4R)-1-acetyl-6-bromo-2-methyl-N-(5-nitro-2-pyridinyl)-1,2,3,4-tetrahydro-4-quinolinamine (for a preparation see Intermediate 19) (4.1 g, 10.12 mmol), {4-[(methyloxy)carbonyl]phenyl}boronic acid (2.185 g, 12.14 mmol), tetrakis(triphenylphosphine)palladium(0) (1.169 g, 1.012 mmol) and potassium carbonate (4.19 g, 30.4 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 then cooled to room temperature and concentrated in vacuo. The residue was partitioned between EtOAc and water and the layers were separated. The organic phase was 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-2-methyl-4-((5-nitropyridin-2-yl)amino)-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (4.3 g, 9.34 mmol, 92% yield) as an orange foam, LCMS (HpH, 2 min), Rt=1.13 min, MH+=461.

Provenance & Evidence