4-Nitrobenzoic Acid → HCID 178464930, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [1-(cis-3-hydroxy-cyclobutyl)-ethyl]-amide (200 mg, 0.37 mmol) in THF (4 mL) was added 4-nitrobenzoic acid (124 mg, 0.74 mmol) and triphenylphosphine (204 mg, 0.78 mmol). Then the reaction mixture was cooled to 0° C. and diethyl azodicarboxylate (123 μL, 0.78 mmol) was added dropwise. The reaction was stirred at room temperature overnight then diluted with CH2Cl2 (25 mL) and washed with 1.0 M aqueous NaOH. The aqueous phase was back-extracted with CH2Cl2 then the combined organics were dried over MgSO4 and concentrated. The residue was absorbed onto SiO2 and purified via chromatography with 20% to 80% EtOAc/hexanes to provide 250 mg (98%) of 4-nitrobenzoic acid trans-3-(1-{[2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-amino}-ethyl)-cyclobutyl ester as a white solid.

Provenance & Evidence