Triethylamine → Ethyl 4-(4-fluorophenylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

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Reaction Conditions

Reaction Steps

Intermediate 1 (0.051 g) and 4-fluoroaniline (0.024 g) were suspended in ethanol (2 ml) and triethylamine (0.14 ml) was added. The mixture was stirred under nitrogen and heated at 80° C. for 16 h. After cooling to room temperature, ethanol was removed by evaporation under a stream of nitrogen and the residue partitioned between DCM and water. The organic layer was loaded directly onto an SPE cartridge (silica, 5 g) and eluted sequentially with; (i) DCM, (ii) DCM: Et2O (2:1), (iii) DCM:Et2O (1:1), (iv) Et2O, (v) EtOAc, (vi) MeOH. Fractions containing desired material were combined and concentrated in vacuo to afford Intermediate 6 (0.077 g). LCMS showed MH+=328; TRET=3.36 min.

Provenance & Evidence