Potassium Phosphate, Tribasic → Methyl 2-(4-methylphenyl)-6-(prop-1-en-2-yl)pyridine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of palladium(II) acetate (21.8 mg, 0.10 mmol) and tris(2-methoxyphenyl)phosphine (68.4 mg, 0.19 mmol) in THF (1 mL) was added a degassed mixture of methyl 2,6-dichloroisonicotinate (250 mg, 1.21 mmol), tripotassium phosphate (386 mg, 1.82 mmol), and 2-isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.285 mL, 1.52 mmol) in THF (1.5 mL) and water (0.625 mL). The mixture was heated to 63° C. After 4 h, a degassed solution of 4-methylphenylboronic acid (247 mg, 1.82 mmol) in THF (1.25 mL) was added. The resulting mixture was heated to 63° C. After 18 h, 4-methylphenylboronic acid (247 mg, 1.82 mmol), palladium(II) acetate (21.8 mg, 0.10 mmol), and tris(2-methoxyphenyl)phosphine (68.4 mg, 0.19 mmol) were added. The resulting mixture was heated to 63° C. After 18 h, the mixture was cooled to ambient temperature. Saturated aqueous NaHCO3 was added and the mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by reverse phase chromatography (C-18, 80% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (191 mg). MS 268.1 (M+1).

Provenance & Evidence