Cesium carbonate → N-[4-(3-fluoro-4-nitro-anilino)-2-pyridyl]cyclopropanecarboxamide

Participants

Reaction Conditions

Reaction Steps

Under N2, mix N-(4-bromo-2-pyridyl)cyclopropanecarboxamide (460 mg, 1.9 mmol), 3-fluoro-4-nitroaniline (359 mg, 2.3 mmol), palladium(II) acetate [Pd(OAc)2, 43.2 mg, 0.19 mmol], 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos, 158 mg, 0.38 mmol), Cs2CO3 (1.2 g, 3.8 mmol) and anhydrous toluene (10 mL). Stir the mixture at 120° C. under N2 for 16 hrs. Cool to room temperature, pour the reaction mixture to water (50 mL), extract with EtOAc (15 mL×3), combine the organic layers and dry over anhydrous Na2SO4. Concentrate under reduced pressure to give the crude product. Purification by chromatography (silica gel, PE:EtOAc=54:46) affords the target compound (160 mg, 22%). MS: (M+1): 317.2.

Provenance & Evidence