Cesium carbonate → (r)-4-(4,5-Dimethyl-6-pyridin-2-ylmethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2h-[1,2']bipyrazinyl-5'-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

(R)-4-(6-Chloro-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H [1,2′]bipyrazinyl-5′-carboxylic acid methyl ester (250 mg, 0.663 mmol) is combined with 2,4-dimethyl-3-pyridin-2-ylmethyl-pentan-3-ol (114.6 mg, 0.553 mmol), cesium carbonate (216.2 mg, 0.664 mmol), palladium triflate (6.2 mg, 0.028 mmol), tricyclohexyl phosphine (15.5 mg, 0.055), and toluene (2 mL). The reaction mixture is heated to 110° C. for 65 h to reach 10% conversion. Add H2O and extract with EtOAc. Concentrate combined organics in vacuo. The residue is purified by flash chromatography on silica gel (MeOH/CH2Cl2) to afford the title compound (13 mg, 5.4%).

Provenance & Evidence