Pyridine, 2,4,6-trichloro- → 2,4-Dichloro-6-(4-isopropoxyphenyl)pyridine

Participants

Reaction Steps

To a 40 mL vial equipped with a stir bar was added 2,4,6-trichloropyridine (1.00 g, 5.48 mmol), (4-isopropoxyphenyl)boronic acid (1.00 g, 5.56 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (“Pd(dppf)Cl2”, 200 mg, 0.273 mmol), and K3PO4 (3.49 g, 16.4 mmol). The vial was sealed with a septum screwcap and then placed under N2 atmosphere. To the vial was added degassed THF (30 mL). The vial was placed in a 60° C. heating block with stirring for 60 hours. To the mixture was added diatomaceous earth (Celite®). The mixture was filtered and the filtrate was concentrated in vacuo to afford an amber solid residue. This material was subjected to silica gel chromatography (hexanes:CH2Cl2) to afford 2,4-dichloro-6-(4-isopropoxyphenyl)pyridine as a colorless oil that solidified upon standing (710 mg, 46%). 1H-NMR: (400 MHz, CDCl3) δ 7.95-7.90 (m, 2H), 7.58 (d, J=1.5 Hz, 1H), 7.22 (d, J=1.5 Hz, 1H), 6.99-6.93 (m, 2H), 4.64 (spt, J=6.1 Hz, 1H), 1.38 (d, J=6.0 Hz, 6H); MS: MS m/z 281.9 (M++1).

Provenance & Evidence