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With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 120℃; for 18.0h;
To a 10% aqueous solution of dioxane (0.1 M) was added 4,6-dichloropyridin-2-amine (1.0 equiv.), trimethylboroxine (1.5 equiv.), Pd(PPh3)4 (0.10 equiv.) and K2CO3 (3.0 equiv.). The solution was heated in an oil bath to 120 C. for 18 hrs, cooled to room temperature (not all of starting material was consumed), extracted with EtOAc, dried with Na2SO4, and concentrated. The crude material was purified via SiO2 column chromatography eluting with 5% MeOH/DCM to yield 4-chloro-6-methylpyridin-2-amine as an off-white solid in 23% yield. LCMS (m/z): 143 (MH+); LC Rt=1.11 min.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 100℃; for 18.0h;
A suspension of 4,6-dichloropyridin-2-amine (1.63 g, 10 mmol), methylboronic acid (0.6 g, 10 mmol), Cs2C03 (9.75 g, 30 mmol), and Pd(dppf)Cl2 (400 mg) in dioxane/water (4: 1, 50 mL) was stirred for 18 hours at 100 C. The reaction was diluted with water and extracted with EtOAc (50 mLx3). The combined organic layer was washed with water and brine. The resulting solution was concentrated under reduced pressure and the residue was purified via prep-HPLC to afford 4-chloro-6-methylpyridin-2-amine (100 mg) as brown solid. MS ESI calcd. For C6H7C1N2 [M + H]+ 143, found 143.
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