Propanedioic acid, monoethyl ester → HCID 86724156, compound

Participants

Reaction Steps

A flask was charged with methyl 4-(1-(5-chloro-1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-4-methoxy-4-oxobutyl)-3-methylbenzoate (2.20 g, 4.98 mmol), potassium; ethoxycarbonyl-acetate (1.70 g, 9.96 mmol), N,N-dimethylpyridin-4-amine (0.608 g, 4.98 mmol), dicyclohexyl-(2′,6′-diisopropoxy-biphenyl-2-yl)-phosphane (0.836 g, 1.79 mmol) and allylpalladium(II) chloride (0.219 g, 0.597 mmol). The flask was evacuated and backfilled with Argon. Mesitylene (13.2 mL) was added then the mixture was stirred at rt for about 10 min under Argon. The mixture was heated at about 120° C. for about 16 h, allowed to cool to rt then filtered. The filter cake was rinsed with EtOAc (20 mL). The filtrate was concentrated in vacuo. The residue was semi-purified by column chromatography (SiO2, 10-30% EtOAc/heptane) to give crude methyl 4-(1-(5-(2-ethoxy-2-oxoethyl)-1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-4-methoxy-4-oxobutyl)-3-methylbenzoate (1.23 g, 50%). The material was used as such in the next step: LC-MS (Table 1, Method g) Rt=2.44 min, m/z 494 (M+H)+.

Provenance & Evidence