Potassium Carbonate → 4-Chloro-2-methylpyridin-3-amine

Participants

Reaction Conditions

Reaction Steps

Following a modified synthetic procedure reported in WO 2005/016892, a mixture of 2-bromo-4-chloropyridin-3-amine (prepared as described in US2002/0119982) (1.0 eq.), trimethylboroxine (1.05 eq.), K2CO3 (3.5 eq.) and PdCl2(dppf)-CH2Cl2 adduct (0.1 eq.) in 10:1 solution 1,4-dioxane:H2O (0.28M) was put in a 10-mL glass vial equipped with a small magnetic stirring bar. The reaction vessel was fitted with a rubber septum, was evacuated and back-filled with argon and sealed with an aluminum/Teflon crimp top. The reaction mixture was then irradiated for 1 h at 120° C., using an irradiation power of 100 W. After completion of the reaction, the vial was cooled to 50° C. with air jet cooling before it was opened. The reaction mixture was diluted with EtOAc and filtered on a pad of Solca Floc®200FCC. The crude product was purified by flash chromatography eluting with 5-100% EtOAc/petroleum ether affording the titled compound as violet oil. MS (ES) C6H7ClN2 requires: 142, found: 143, 145 (M+H)+.

Provenance & Evidence