CNC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl.Cc1nn(C)cc1N>C1CCCC1.CC(=O)O.CC(=O)O.CC(C)(C)[O-].CC(C1CCCC1P(C1CCCCC1)C1CCCCC1)P(C(C)(C)C)C(C)(C)C.COCCOC.[Fe].[Na+].[Pd]>CNC(=O)c1ccccc1Nc1cc(Nc2cn(C)nc2C)ncc1Cl1,3-dimethyl-1H-pyrazol-4-amine (180 mg, 1.62 mmol), 2-(2,5-dichloropyridin-4-ylamino)-N-methylbenzamide (400 mg, 1.35 mmol), Sodium t-Butoxide (156 mg, 1.62 mmol),(R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T- BUTYLPHOSPHINE (73.8 mg, 0.14 mmol) and diacetoxypalladium (24.26 mg, 0.11 mmol) were suspended in DME (8 mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 30 minutes in the microwave reactor and cooled to RT. Incomplete reaction, the reaction was heated to 150 °C for a further 1 hour in the microwave reactor and cooled to RT. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and fractions were evaporated to dryness. The crude product was then purified by Basic prep HPLC, fractions containing the desired compound were evaporated to dryness to afford 2-(5-chloro-2-(1,3-dimethyl-1H-pyrazol-4-ylamino)pyridin-4-ylamino)-N-methylbenzamide (267 mg, 53.3 %) as a brown solid.
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