Potassium Carbonate → HCID 86669271, compound

Participants

Reaction Steps

2-bromo-5-(1-piperidinylmethyl)pyridine (for a preparation see Intermediate 24) (98 mg, 0.384 mmol) was mixed with 1-methylethyl[(cis)-1-acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Intermediate 12) (100 mg, 0.240 mmol), potassium carbonate (66.4 mg, 0.480 mmol) and tetrakis(triphenylphosphine)palladium(0) (13.88 mg, 0.012 mmol), dissolved in ethanol (1 mL) and toluene (1 mL) and stirred under nitrogen at 90° C. The reaction mixture was loaded onto a 5 g SCX column, eluting with MeOH (30 mL) followed by 2M MeOH/NH3 (30 mL). Product-containing fractions were evaporated to dryness to give a yellow solid (155 mg). This was purified by MDAP. Product-containing fractions were evaporated to dryness to give a clear, colourless solid (55 mg). LCMS (Method C): Rt=0.67, MH+=465

Provenance & Evidence