Carbamate → HCID 67439726, compound

Participants

Reaction Conditions

Reaction Steps

A substituted aniline was N-protected with a formyl, Boc or similar amide or carbamate protecting group using a standard method. Subsequently, this N-protected aniline derivative was dissolved in DMF (under N2), cooled to 0° C. and added NaH (1.1 eq). After stirring for 30 min at rt, 2-fluoropyridine was added to the reaction mixture and stirring was continued at 70° C. for 1-3 days. After cooling to rt, aqueous saturated NaHCO3 was added and the mixture extracted with EtOAc. The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo to give the crude product which was purified by preparative LC-MS or by column chromatography to give the desired N-protected N-phenyl-2-aminopyridine. After a reaction step to remove the N-protecting group, using a standard method, the obtained phenyl-pyridin-2-yl-amine was dissolved in acetonitrile (under N2) in a closed vial and added the required halide for the N-alkylation. The reaction mixture was then heated to 100-150° C. for 30-720 min using MW irradiation. After cooling to rt, the crude product could be isolated upon aqueous basic work-up and subsequently purified by preparative LC-MS or, alternatively, by column chromatography and/or recrystallization to give the desired N,N′-disubstituted 2-aminopyridine.

Provenance & Evidence