1,2-Dimethoxyethane → Tert-Butyl-[5''-(3-methoxy-phenyl)-[2,2';4',3'']terpyridin-6'-yl]-amine

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Reaction Steps

To a solution of 3-Methoxy boronic acid (1.2 eq, 0.252 mmol, 32 mg) and 2M Na2CO3 (1 eq, 0.21 mmol, 0.1 ml) in dry DME (1 ml) under an inert atmosphere of argon are added (5″-Bromo-[2,2′;4′,3″]terpyridin-6′-yl)-tert-butyl-amine (Example 2.48; Step 1) (1 eq, 0.21 mmol, 80 mg) and PdCl2dppf (0.1 eq, 0.021 mmol, 15 mg). The reaction mixture is heated using microwave radiation at 90° C. for 2 hours 30 mins. The reaction mixture is dissolved in DCM and washed with water. The organic solvent is reduced in vacuo and the residue is purified by reverse phase chromatography (Isolute™ C18, 0-40% 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 and 2M NH3 in MeOH. The methanolic ammonia fractions are combined, concentrated in vacuo and dried under vacuum to afford the title compound; [M+H]+ 411.

Provenance & Evidence