2-Fluoro-4-methyl-5-nitropyridine

White powder

(1779) Under inert atmosphere, to a solution of tert-butyl ethyl malonate (2.43 ml_, 12.82 mmol) in tetrahydrofuran (42 ml.) at 0 C sodium hydride (60% in mineral oil, 512 mg, 12.82 mmol) was added portionwise. The mixture was stirred at 0 C for 30 min, then (1 mmol) was added to a 25 ml reaction tube.Phenylhydrazine hydrochloride (2 mmol), sodium tert-butoxide (3 mmol), H2O (0.5 mL) and toluene (2.5 mL). The reaction was carried out at 130 C.The reaction time was 28 hours, and after the reaction was completed, it was cooled to room temperature.The reaction was quenched by adding 10 mL of ethyl acetate, and washed with 6 mL of saturated brine.The organic phase was separated, and the aqueous phase was extracted three times with ethyl acetate (6 mL of ethyl acetate each time). The organic phase was combined, dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure, including organic solvent and inorganic solvent. Said organic solvent, and then separated by column chromatography to obtain the target product, The yield was 95%.To a solution of cyclobutanol (2 g, 28.8 mmol), Cs2C03 (12.5 g, 38.4 mmol) in ACN (19.2 mL) was added dropwise 2-fluoro-4-methyl- 5-nitropyridine (3 g, 19.2 mmol). The reaction mixture was stirred at rt for 20 h. H2O (300 mL) and DCM (200 mL) were added to the reaction mixture. The reaction mixture was extracted with DCM. The combined organics were separated, dried (Na2SC>4), filtered, and concentrated under reduced pressure. The crude title Compound, as a red oil, was used without further purification.To a solution of cyclobutanol (2 g, 28.8 mmol), Cs2CO3 (12.5 g, 38.4 mmol) in ACN (19.2 mL) was added dropwise General procedure: The synthesis of 3-methyl-5-nitro-2-(2-phenylhydrazinyl)pyridine (PH5N3M) was performed in the following way: 0.01 mol of 2-fluoro-3-methyl-5-nitropyridine was dissolved in10 cm3 of methanol and 0.02 mol of phenylhydrazine was added to this solution. The obtained mixture was heated for 1-2 min at 60 C and left at room temperature for 24 h. Next, the solvent was distilled off under reduced pressure and the residue was extracted with hot chloroform. Insoluble hydrofluoride phenylhydrazine was filtered and washed with warm chloroform.

Molecular Weight:156.11
XLogP3:1.5
Hydrogen Bond Acceptor Count:4
Exact Mass:156.03350557
Monoisotopic Mass:156.03350557
Topological Polar Surface Area:58.7
Heavy Atom Count:11
Complexity:159
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes