Diisopropylamine → Methyl 3-(5-methylpyridin-2-yl)-5-(2-methylpyrimidin-5-yl)benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-(5-methylpyridin-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (170 mg, 0.481 mmol) in N,N-dimethylformamide (1.44 mL) and water (0.481 mL) was added 5-bromo-2-methylpyrimidine (167 mg, 0.963 mmol), palladium(II) acetate (5.40 mg, 0.024 mmol), 3,3′3″-phosphinidynetris(benzenesulfonic acid)trisodium salt (41.0 mg, 0.072 mmol) and diisopropylamine (0.171 mL, 1.20 mmol) and the mixture was heated to 80° C. After 1 h, the reaction was allowed to cool to ambient temperature and filtered. Purification by reverse phase chromatography (C-18, 95% water/acetonitrile→50% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (100 mg). MS 320.1 (M+1).

Provenance & Evidence