Triethylamine → 4-(2-Fluoro-4-nitrophenoxy)-2-[(pyrrolidin-1-yl)carbonylamino]pyridine

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Reaction Steps

4-(2-fluoro-4-nitrophenoxy)pyridin-2-amine (0.150 g, 0.60 mmol) was dissolved in THF (10 ml). Then triethylamine (0.17 ml, 1.2 mmol) was added to the mixture while stirring. Then phenyl chloroformate (0.15 ml, 1.2 mmol) was added to the mixture dropwise. The mixture was stirred at ambient temperature for 1.5 hours. Then pyrrolidine (0.50 ml, 6.0 mmol) was added to the mixture and stirred an additional 30 minutes. The mixture was diluted with sat. ammonium chloride (10 ml) and dichloromethane (10 ml) and stirred 10 minutes and was collected by extracted with dichloromethane (3×10 ml). The organic layer was dried over sodium sulfate, filtered, and concentrated in-vacuo. The crude was purified by chromatography (Amino-Propyl silica gel column) in a gradient of 1-5% MeOH/dichloromethane to give the desired product N-(4-(2-fluoro-4-nitrophenoxy)pyridin-2-yl)pyrrolidine-1-carboxamide (0.184 g, 0.53 mmol, 88% yield) as tan oil. MS (ESI pos. ion) m/z: 347 (MH+). Calc'd exact mass for C16H15FN4O4: 346. 1HNMR (300 MHz, CDCl3): 1.96 (s, 4H), 3.44 (t, J=6.65 Hz, 4H), 6.81-6.96 (m, 2H), 8.06-8.18 (m, 4H).

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