Potassium Carbonate → HCID 67194734, compound

Participants

Reaction Steps

A flask was charged with 1-methylethyl (1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate (for a preparation see Example 61) (100 mg, 0.271 mmol), potassium carbonate (74.9 mg, 0.542 mmol), 2-(dihydroxyboranyl)-3-furancarboxylic acid (50.7 mg, 0.325 mmol) and tetrakis(triphenylphosphine)palladium(0) (15.65 mg, 0.014 mmol) then filled with ethanol (1 mL) and toluene (1 mL) and the resulting mixture was refluxed under nitrogen for 21 h then cooled to room temperature and partitioned between a 2M HCl aqueous solution (40 mL) and EtOAc (40 mL). The layers were separated and the aqueous phase was extracted with EtOAc (2×40 mL). The combined organic phases were washed with brine (80 mL), dried over Na2SO4 and concentrated in vacuo. Purification of the residue using MDAP (modifier; trifluoroacetic acid) gave a residue which was treated with a 2M NaOH aqueous solution (2.25×10−2 mL, 4.50 mmol). The precipitate formed was filtered off and dried under house vacuum to give sodium 2-[(2R,4S)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-3-furancarboxylate (18 mg, 0.040 mmol, 15%) as a cream solid.

Provenance & Evidence