Sodium Carbonate → 3-(6'-Methylamino-[2,2';4',3'']terpyridin-5''-yl)-phenol

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Reaction Steps

To a solution 3-Hydroxphenolboronic acid, pinacol ester (2.0 eq, 1.172 mmol, 0.258 g) and 2M Na2CO3 (2.0 eq, 1.172 mmol, 0.586 ml) in DME (2.5 ml) is added (5″-Bromo-[2,2′;4′,3″]terpyridin-6′-yl)-methyl-amine (Example 2.1; step1) (1 eq, 0.586 mmol, 0.200 g) followed by [1,1′-Bis(diphenylphosphino)-ferrocene]dichloropalladium (II), complex with DCM (0.1 eq, 0.059 mmol, 0.048 g). The reaction mixture is heated using microwave radiation at 90° C. for 90 mins. The reaction mixture is dissolved in DCM 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 flash chromatography (0-100% EtOAc in iso-hexane and up to 10% MeOH in EtOAc), to yield intermediate to afford the title compound; [M+H]+ 355.

Provenance & Evidence