Cc1c(Cl)c2cc(N)ccc2n1C.Cc1nn(-c2ccnc(Cl)n2)cc1C=O>C1COCCO1.CC(=O)O.CC(=O)O.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.O=C([O-])[O-].[K+].[K+].[Pd]>Cc1nn(-c2ccnc(Nc3ccc4c(c3)c(Cl)c(C)n4C)n2)cc1C=OA 40 mL scintillation vial charged with 3-chloro-1,2-dimethyl-1H-indol-5-amine (192 mg, 0.99 mmol), 1-(2-chloropyrimidin-4-yl)-3-methyl-1H-pyrazole-4-carbaldehyde (200mg, 0.90 mmol), palladium(II) acetate (10.08 mg, 0.04 mmol), dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine (x--phos) (42.8 mg, 0.09 mmol) and Dioxane (8mL) After being degassed by nitrogen bubbling , the reaction mixture was heated 100 °C for 6 hours. At this stage most of the starting material was consumed. The reaction mixture was diluted with ethyl acetate (50 mL) and washed with water and brine. The organic layer separated, dried over sodium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography (Isco, Hexane/ethyl acetate, 0-100%, 25 minutes) to give 1-(2-((3-chloro-1,2-dimethyl-1H-indol-5-yl)amino)pyrimidin-4-yl)-3-methyl-1H-pyrazole-4-carbaldehyde (221 mg, 64.6 %) as a yellow solid. LC/MS (2 minute, Acid _CV10.olp method) 381 (M + 1), 1.27 minutes.
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