HCID 58961588, compound → HCID 10309568, compound

Participants

Reaction Steps

To a solution of methyl 2-chloro-6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyridine-3-carboxylate (750 mg, 1.76 mmol) from Step A in methanol (10 mL) and ethyl acetate (10 mL) was added 10% Pd/C (100 mg). The suspension was stirred under an atmosphere of hydrogen (balloon pressure) for 45 min and was then filtered to remove the catalyst. HPLC/MS indicated a mixture of starting material, desired product, and minor amounts of several possible phenyl ring dechlorination products. The filtrate was evaporated and the residue was purified by flash column chromatography on silica gel eluted with 5 to 20% ethyl acetate in hexanes. The fractions containing the title compound were repurified by preparative TLC eluted with 15% ethyl acetate in hexanes to give pure methyl 6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyridine-3-carboxylate. HPLC/MS: 392 (M+1), 394 (M+3); Rt=4.29 min. 1HNMR (CDCl3): δ 4.024 (s, 3H), 7.11 (br d, J=8.6 Hz, 2H), 7.23-7.35 (m, 4H), 7.36 (d, J=2.0 Hz, 1H), 7.37 (d, J=1.9 Hz,, 1H), 9.286 (d, J=1.9 Hz, 1H).

Provenance & Evidence