Sodium Carbonate → HCID 68763594, compound

Participants

Reaction Steps

To a solution of 1-Methyl-4[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-phenyl]-piperazine (1.2 eq, 0.083 mmol, 0.025 g) and 2M Na2CO3 (4.0 eq, 0.138 mmol, 0.1 ml) in DME (1 ml) is added Benzyl-(5″-bromo-6-methyl-[2,2′;4′,3″]terpyridin-6′-yl)-amine (Example 2.40; step1) (1 eq, 0.069 mmol, 0.03 g) followed by [1,1′-Bis(diphenylphosphino)-ferrocene]dichloropalladium (II), complex with DCM (0.1 eq, 0.0069 mmol, 5 mg). The reaction mixture is heated using microwave radiation at 90° C. for 1 hour 15 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 reverse phase column chromatography (Isolute™ C18, 0-50% 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 2M NH3 in MeOH. The methanolic ammonia fractions are combined, concentrated in vacuo and dried under vacuum to afford the title compound; [M+H]+ 527.

Provenance & Evidence