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Structure of 1075756-90-9

Chemical Structure| 1075756-90-9

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Product Details of [ 1075756-90-9 ]

CAS No. :1075756-90-9
Formula : C7H5F2NO
M.W : 157.12
SMILES Code : CC(=O)C1=NC=C(F)C=C1F
MDL No. :MFCD18711444
InChI Key :DLGIFMVJOGACLY-UHFFFAOYSA-N
Pubchem ID :55282576

Safety of [ 1075756-90-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 1075756-90-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1075756-90-9 ]

[ 1075756-90-9 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 298709-29-2 ]
  • [ 75-16-1 ]
  • [ 1075756-90-9 ]
YieldReaction ConditionsOperation in experiment
A solution of methylmagnesium bromide (36.8 ml, 117.78 mmol) in THF (50ml) was stirred under N2 and cooled to -780C. 3,5-difiuoropicolinonitrile (15.0 g, 107.07 mmol) in THF (50 ml) was added drop wise with an addition funnel at such a rate that the internal temperature was kept below -40C. After the addition was complete, the reaction mixture was poured into a IM HCl (100 ml, chilled in an ice bath). The reaction mixture was stirred at O0C for 30 minutes and at room temperature for 30 minutes. To this solution 150 ml of EtOAc was added to extract product. The aqueous phase was neutralized to pH9 with NaHCO3 and extracted with EtOAc (2 X 20 ml). The organic layers were combined and the volatiles were removed under reduced pressure. Purification utilizing ISCO (0-10percent EtOAc- hexanes) gave the title compound as light yellow oil. LC-MS: 158 [M+H]+.
Intermediate 33 ; l-(3,5-Difluoropyridin-2-yl)ethanoneA solution of methylmagnesium bromide (36.8 ml, 117.78 mmol) in THF (50ml) was stirred under N2 and cooled to -780C. <strong>[298709-29-2]3,5-difluoropicolinonitrile</strong> (15.0 g, 107.07 mmol) in THF (50 ml) was added drop wise with an addition funnel at such a rate that the internal temperature was kept below -40C. After the addition was complete, the reaction mixture was poured into a IM HCl (100 ml, chilled in an ice bath). The reaction mixture was stirred at O0C for 30 minutes and at room temperature for 30 minutes. To this solution 150 ml of EtOAc was added to extract product. The aquous phase was neutralized to pH9 with NaHCO3 and extracted with EtOAc (2 x 20 ml). The organic layers were combined and the volatiles were removed under reduced pressure. Purification utilizing ISCO (0-10percent EtOAc- hexanes) gave the title product as light yellow oil. LC-MS: 158 [M+H]+.
Intermediate 45 l-(3,5-Difluoropyridin-2-yr)ethanoneA solution of methylmagnesium bromide (36.8 ml, 117.78 mmol) in THF (50ml) was stirred under N2 and cooled to -78°C. <strong>[298709-29-2]3,5-difluoropicolinonitrile</strong> (15.0 g, 107.07 mmol) in THF (50 ml) was added drop wise with an addition funnel at such a rate that the internal temp, was kept below -4°C. After the addition was complete, the reaction was poured into a IM HCl (100 ml, chilled in an ice bath). The reaction was stirred at 00C for 30 minutes and r.t. for 30 minutes. To this solution 150 ml of EtOAc was added to extract product. The aqueous phase was neutralized to pH9 with NaHCO3 and extracted with EtOAc (2 X 20 ml). The organic phase were combined and the volatiles were removed under reduced pressure. Purification by ISCO (0-10percent EtOAc- hexanes) gave the title compound as light yellow oil. LC-MS: 158 [M+H].
A solution of methylmagnesium bromide (36.8 ml, 117.78 mmol) in THF (50ml) was stirred under N2 and cooled to -78°C. 3,5-Difluoropicolinonitrile (15.0 g, 107.07 mmol) in THF (50 ml) was added drop wise with an addition funnel at such a rate that the internal temperature was kept below -4°C. After the addition was complete, the reaction mixture was poured into a IM HCl (100 ml, chilled in an ice bath). The reaction mixture was stirred at 00C for 30 minutes and room temperature for 30 minutes. To this solution 150 ml of EtOAc was added to extract product. The aqueous phase was neutralized to pH 9 with NaHCO3 and extracted with EtOAc (2 X 20 ml). The organic layers were combined and the volatiles were removed under reduced pressure. Purification by ISCO (0-10percent EtOAc- hexanes) gave the title product as light yellow oil. <n="82"/>LCMS: 158 [M+H]
To a solution of <strong>[298709-29-2]3,5-difluoropicolinonitrile</strong> (10.0 g, 71.4 mmol) in THF (200 ml) was added methylmagnesium bromide (61.2 ml, 85.7 mmol) in THF solution at 0 0C. The reaction was stirred at room temperature for 1.5 hours. Saturated sodium bicarbonate solution (50 ml) was added, extracted with ether (100 ml), and dried over sodium sulfate. The solvent was removed. The residue (11.2 g, 71.28 mmol), hydroxylamine hydrochloride (9.907 g, 142.6 mmol) and sodium acetate (11.70 g, 142.6 mmol) in EtOH (100 ml) and water (50 ml) was heated at reflux for 3 hours. The solvent was removed and diluted with 50 ml of saturated sodium bicarbonate and extracted with EtOAc (2 x 200 ml). After dried over sodium sulfate, the solvent was removed and the title compound was used directly in next step without purification.

 

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