CNC(=O)c1ccccc1N.Clc1cc(I)c(Cl)cn1>C1COCCO1.CC(=O)O.CC(=O)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C([O-])[O-].[Cs+].[Cs+].[Pd]>CNC(=O)c1ccccc1Nc1cc(Cl)ncc1ClPalladium(II) acetate (0.098 g, 0.44 mmol) was added to 2,5-dichloro-4-iodopyridine (3 g, 10.95 mmol), 2-amino-N-methylbenzamide (1.645 g, 10.95 mmol), Cesium carbonate (7.14 g, 21.91 mmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (0.380 g, 0.66 mmol) in dioxane (150 mL) under nitrogen. The resulting suspension was stirred at 80 °C for 18 hours. The reaction mixture was filtered and the filtrate was evaporated to dryness. The crude residue was triturated with DCM to give a solid which was collected by filtration and dried under vacuum to give 2-(2,5-dichloropyridin-4-ylamino)-N-methylbenzamide (1.58 g, 49 %) as a tan solid, LCMS indicated 87% pure. This was purified by flash silica chromatography, elution gradient 0 to 5% MeOH in DCM. Pure fractions were evaporated to dryness to afford 2-(2,5-dichloropyridin-4-ylamino)-N-methylbenzamide (1.040 g, 32.1 %) as a yellow solid.
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