Dimethylformamide → HCID 68764339, compound

Participants

Reaction Conditions

Reaction Steps

A 50 mL round bottom flask charged with tert-butyl 4-(5-cyclopropyl-3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (500 mg, 0.85 mmol), triethylamine (355 μL, 2.54 mmol), Pd2dba3 (19.4 mg, 0.021 mmol), tri-o-tolylphosphine (19.4 mg, 0.064 mmol), and DMF (7 mL) was purged under N2 (3 cycles). 3-vinylpyridine (270.24 mg, 1.7 mmol) was added, and the mixture was stirred at 100° C. under a N2 atmosphere for 6 hours. The reaction mixture was cooled to room temperature, diluted with warm EtOAc (100 mL) and washed with water (2×30 mL). The phases were separated, and the organic layer was dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (Biotage Flash 40S+) eluting with 25% EtOAc/hexane followed by 50% EtOAc/hexane to provide (E)-tert-butyl 4-(5-cyclopropyl-1-(4-methoxybenzyl)-3-(2-(pyridin-3-yl)vinyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (390 mg, 81% yield) as a solid. LCMS (APCI+) m/z 567.3 (M+H)+.

Provenance & Evidence