Sodium Carbonate → HCID 86633644, compound

Participants

Reaction Steps

4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazole-1-carboxylic acid tert-butyl ester (1.1 eq, 0.12 mmol, 34 mg) is stirred in NMP (1 ml) and 2M Na2CO3 (2 eq, 0.21 mmol, 0.106 ml) for 15 minutes, under an inert atmosphere of argon. (5″-Bromo-[2,2′;4′,3″]terpyridin-6′-yl)-[2-(1H-indol-3-yl)-ethyl]-amine (Example 1.14) (1 eq, 0.11 mmol, 50 mg) and 1,4-bis(diphenylphosphino)butane-palladium(II) chloride (0.2 eq, 0.021 mmol, 12 mg) are added and the reaction mixture is flushed with argon and heated using microwave radiation at 100° C. for 2 hours. The reaction mixture is extracted into EtOAc washing with water. The organic phase is washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The crude residue is purified by reverse phase column chromatography (Isolute™ C18, 0-50% acetonitrile in water—0.1% TFA) and 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 concentrated in vacuo and dried under vacuum to afford the title compound; [M+H]+ 458.

Provenance & Evidence