Diisopropylethylamine → HCID 44539732, compound

Participants

Reaction Steps

To a solution of 3-chloropicolinic acid (380 mg, 2.42 mmol, available from Fluorochem Ltd.) in DMF (5 ml) was added HATU (920 mg, 2.42 mmol) and DIPEA (1.266 ml, 7.25 mmol). The mixture was stirred at room temperature for 20 mins then 6-(1H-indol-4-yl)-1H-indazol-4-amine (300 mg, 1.21 mmol) was added and the mixture stirred at room temperature overnight. The reaction mixture was concentrated in vacuo to give a volume of approx. 1 ml which was added to the top of a 20 g aminopropyl cartridge that had been preconditioned with MeOH. The reaction mixture remained on the cartridges for 2 h before being eluted with MeOH. The solvent was removed in vacuo to give a brown oil that was purified by chromatography using silica gel (70 g cartridge, FlashMaster II) eluting with 0-25% MeOH in DCM over 30 mins to afford the title compound (130 mg) as a brown solid.

Provenance & Evidence