Dichloromethane → Methyl-{5''-[3-(4-methyl-piperazin-1-ylmethyl)-phenyl]-[2,2';4',3'']terpyridin-6'-yl}-amine

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Reaction Steps

To a solution of 3-((4-Methyl-piperazin-1-yl)methyl)-phenyl boronic acid (Intermediate B1) (1.2 eq, 0.704 mmol, 0.165 g) and 2M Na2CO3 (2.0 eq, 1.17 mmol, 0.6 ml) in DME (3 ml) is added (5″-Bromo-[2,2′;4′,3″]terpyridin-6′-yl)-methyl-amine (Example 2.1; step1) (1 eq, 0.586 mmol, 0.2 g) followed by [1,1′-Bis(diphenylphosphino)-ferrocene]dichloropalladium (II), complex with DCM (0.1 eq, 0.058 mmol, 0.043 g). The reaction mixture is heated using microwave radiation at 90° C. for 4 hours. The reaction mixture is dissolved in EtOAc and washed with water. The organic layer is washed with brine, dried over drying agent MgSO4, filtered and the organic solvent is reduced in vacuo. The crude residue is purified by reverse phase column chromatography (Isolute™ C18, 0-20% acetonitrile in water—0.1% TFA). The appropriate fractions by HPLC are combined and concentrated in vacuo. The resulting residue is dissolved in MeOH and loaded onto a SCX-2 cartridge eluting with MeOH followed by 2 M NH3 in MeOH. The methanolic ammonia fractions are combined, concentrated in vacuo and dried under vacuum to afford the title compound; [M+H]+ 451.

Provenance & Evidence