Ethyl 4-[(6-chloropyridin-3-yl)amino]benzoate could be produced through the following synthetic routes.

Ethyl 4-[(6-chloropyridin-3-yl)amino]benzoate. To a 250-mL, one-necked, round-bottomed flask, fitted with a septum pierced with nitrogen inlet and outlet needles, is added Pd(OAc₎₂ (0.135 g, 0.6 mmol), rac. BINAP (0.374 g, 0.6 mmol) and 100 mL of toluene. The mixture is stirred under a nitrogen flow for 15 min. In a 1000 mL round-bottomed, three-necked flask is added 2-chloro-5-iodopyridine (7.183 g, 30 mmol), ethyl 4-aminobenzoate (5.947 g, 36 mmol) and Cs₂CO₃ (48.873 g, 150 mmol). Then, a reflux condenser equipped with a bubbler filled with oil is placed on the three-necked flask and one of the side necks is stoppered. Subsequently, a nitrogen inlet is connected to the remaining neck and the apparatus is flushed with nitrogen for 5 min. Next, under a low flow of nitrogen, the stoppered side neck is opened and the catalyst solution is added through a funnel using 200 mL of toluene to rinse the flask. Under magnetic stirring the resulting mixture is flushed with nitrogen for 10 min. Then, the nitrogen inlet is removed, the neck stoppered and the 1000 mL, three-necked flask placed in a preheated oil bath at 130 °C for 20 h under a nitrogen atmosphere. Vigorous magnetic stirring is required to prevent precipitation of the base. When the reaction mixture is cooled down to room temperature, it is filtered over a sintered glass filter funnel containing Celite® using 1000 mL of EtOAc. The filtrate is concentrated at reduced pressure by rotary evaporation at 45 °C (75 mmHg) to afford a brown oil. The residue is dissolved in a minimal amount of 99:1 CH₂Cl₂:MeOH and loaded on a pre-packed silica gel column (40 × 6 cm, ± 500 g). The 99:1 CH₂Cl₂:MeOH eluent is used to isolate ethyl 4-[(6-chloropyridin-3-yl)amino]benzoate, in addition to fractions mixed with ethyl-4-aminobenzoate. The impure fractions are collected and concentrated at reduced pressure by rotary evaporation at 45 °C (75 mmHg). The resulting dark beige crystals are then dissolved in a minimum amount of dichloromethane and loaded onto a second pre-packed silica gel column (40 × 6 cm, ± 500 g). Pure dichloromethane is used as an eluent until the product begins to elute and subsequently, 99:1 CH₂Cl₂:MeOH is used to afford ethyl 4-[(6-chloropyridin-3-yl)amino]benzoate (7.068 g combined from two purifications, 25.5 mmol, 85%) as a light beige solid.