ChemicalBook CAS DataBase List 2-Cyano-3-fluoropyridine

2-Cyano-3-fluoropyridine synthesis

8synthesis methods

Product Name:2-Cyano-3-fluoropyridine
CAS Number:97509-75-6
Molecular formula:C6H3FN2
Molecular Weight:122.1

695-37-4

7677-24-9

97509-75-6

Using 3-fluoropyridine-N-oxide (Intermediate A, 2.85 g, 25.2 mmol) and trimethylcyanosilane (10.0 mL, 75.6 mmol) as raw materials, Intermediate A was dissolved in dichloromethane (25 ml) at room temperature, followed by addition of trimethylcyanosilane. The reaction mixture was heated to reflux for 10 hours. After completion of the reaction, it was cooled to room temperature and the reaction was quenched by the addition of saturated aqueous sodium bicarbonate solution (30 mL). The reaction mixture was extracted with dichloromethane (3 x 150 mL), the organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the organic phase was concentrated under reduced pressure to give a light brown oily crude product (4.60 g). The crude product was purified by rapid column chromatography on silica gel, the eluent was hexane solution of 30% ethyl acetate to give a light brown oil, which solidified to light brown solid product B (2.48 g, 84% yield) after standing. The product was analyzed by HPLC with a retention time of 1.03 min.

38180-46-0 Synthesis

38180-46-0
252 suppliers
$6.00/1g

97509-75-6
285 suppliers
$8.00/1g

Yield:97509-75-6 442 mg (50%)

Reaction Conditions:

with potassium fluoride in 1-methyl-pyrrolidin-2-one

Steps:

1 3-Fluoropyrid-2-ylamidoxime
A solution of 2-cyano-3-chloropyridine (1 g, 7.22 mmol) in 1-methyl-2-pyrrolidinone (25 mL) was treated with potassium fluoride (1.26 g, 21.68 mmol) and heated at reflux for 18 hours. After cooling, the reaction was diluted with ethyl acetate and extracted with water and brine. Silica gel chromatography afforded 442 mg (50%) of 2-cyano-3-fluoropyridine.

References:

Wagenen, Bradford Van;Stormann, Thomas M.;Moe, Scott T.;Sheehan, Susan M.;McLeod, Donald A.;Smith, Daryl L.;Isaac, Methvin Benjamin;Slassi, Abdelmalik US2003/55085, 2003, A1

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695-37-4
113 suppliers
$60.00/100mg

7677-24-9 Synthesis

7677-24-9
389 suppliers
$19.00/5g

97509-75-6
285 suppliers
$8.00/1g

References

152126-32-4 Synthesis