Dichloromethane → 2-{5''-[4-(4-Isopropyl-piperazin-1-ylmethyl)-phenyl]-[2,2';4',3'']terpyridin-6'-yl}-propan-2-ol

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Reaction Steps

To a solution of 4-((4-isopropyl-piperazin-1-yl)methyl)-phenyl boronic acid (Intermediate B3) (1.2 eq, 0.324 mmol, 0.085 g) and 2M Na2CO3 (2.4 eq, 0.648 mmol, 0.32 ml) in DME (3 ml) is added 2-(5″-bromo-[2,2′;4′,3″]terpyridin-6′-yl)-propan-2-ol (1 eq, 0.27 mmol, 0.1 g) followed by [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium (II), complex with DCM (0.1 eq, 0.027 mmol, 0.022 g). The reaction mixture is heated using microwave radiation at 95° C. for 90 minutes. The reaction mixture is dissolved in EtOAc and washed with water. The organic layer is washed with brine, dried over 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 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 2M NH3 in MeOH. The methanolic ammonia fractions are combined, concentrated in vacuo and dried under vacuum to afford the title compound; [M+H]+ 508.

Provenance & Evidence