2-Amino-5-bromopyridine → Methyl 4-oxo-4-[[5-(3-pyridyl)-2-pyridyl]amino]butanoate

Participants

Reaction Conditions

Reaction Steps

Methyl 4-[(5-bromo-2-pyridyl)amino]-4-oxo-butanoate (Commercially available or prepared as described in example II using as starting material the commercially available: 5-bromo-2-aminopyridine, 200 mg, 0.697 mmol) was dissolved in toluene in a microwave vial and 3-pyridyltributylstannane (0.836 mmol, 0.290 mL) and tetrakis(triphenylphosphine) palladium(0) (0.069 mmol) were added. Argon was bubbling through the mixture for ca. 5 min and the vial was heated under microwave irradiations for 10 min at 150° C. The solvent was evaporated and the residue was diluted with acetonitrile, washed with cyclohexane (2×) and evaporated. The product was purified by flash chromatography (RF-machine, AcOEt/cyclohexane: 0/100→100/0) to give methyl 4-oxo-4-[[5-(3-pyridyl)-2-pyridyl]amino]butanoate (compound A82) (0.051 g, 26% Yield). LC-MS (Method F) RT 0.50, 286 (M+H+). Compound A83, A84 and A85 from table A were prepared by the same method using the corresponding coupling reagent.

Provenance & Evidence