Potassium Phosphate, Tribasic → HCID 66840971, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2.6 g (4.88 mmol) of methyl 6-[3-[(4-methoxybenzyl)oxy]-4-chlorophenyl]-5-{[(trifluoromethyl)sulfonyl]oxy}pyridine-2-carboxylate (Example 1.4) and 880 mg (6.48 mmol) of 2-methylphenylboronic acid in 20 mL of anhydrous DMF is stirred for 15 minutes while sparging with argon, followed by addition of 1.27 g (6 mmol) of anhydrous K3PO4 and 0.58 g (0.5 mmol) of Pd(PPh3)4, and the reaction mixture is stirred for 18 hours at 90° C. under argon. The reaction medium is then poured at room temperature into 120 ml of a 1/1/2 ether/EtOAc/water mixture. After extracting, the aqueous phase is re-extracted with 10 mL of EtOAc, the organic phases are combined and washed with 4×30 mL of water, dried over Na2SO4 and then concentrated under reduced pressure. The residue obtained is purified by chromatography on a column of silica gel, eluting with a heptane/EtOAc gradient of from 0 to 20% EtOAc. After concentrating under reduced pressure, 1.8 g of methyl 6-[3-[(4-methoxybenzyl)]oxy-4-chlorophenyl]-5-(2-methylphenyl)pyridine-2-carboxylate are obtained in the form of an oil.

Provenance & Evidence