3-CYANO-5-FLUOROPYRIDINE synthesis
- Product Name:3-CYANO-5-FLUOROPYRIDINE
- CAS Number:696-42-4
- Molecular formula:C6H3FN2
- Molecular Weight:122.1
70-58-6
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696-42-4
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Yield: 86.3%
Reaction Conditions:
with triethylamine;trifluoroacetic anhydride in dichloromethane at 15; for 12 h;Inert atmosphere;
Steps:
22.3 ] Step 3 : 5-Fluoropyridine-3-carbonitrile
To a mixture of 5-fluoropyridine-3-carboxamide (6 g, 42.39 mmol, 1 eq) and TEA (6.43 g, 63.59 mmol, 8.85 mL, 1.5 eq) in DCM (60 mL) was added TFAA (13.36 g, 63.59 mmol, 8.85 mL, 1.5 eq) dropwise at 15 °C under N2 The mixture was stirred at 15 °C for 12 h. TLC (PE/EA = 1/1, Rf = 0.89) indicated the starting material was consumed completely and one new spot formed. The reaction mixture was concentrated under reduced pressure to give a residue which was purified by flash silica gel chromatography (ISCO; 24 g SepaFlash Silica Flash Column, Eluent of 0-20% Ethyl acetate/Petroleum ethergradient 30 mL/min) to yield 5-fluoropyridine-3-carbonitrile (4.7 g, 36.57 mmol, 86.3% yield, 95.0% purity) as a white solid. NMR (400 MHz, CD3OD) δ ppm 8.82-8.71 (m, 2H), 8.14-8.06 (m, 1H); ES-LCMS: No correct mass was found.
References:
KYN THERAPEUTICS;CASTRO, Alfredo C.;EVANS, Catherine Anne WO2018/195397, 2018, A2 Location in patent:Paragraph 00345; 00348
557-21-1
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407-20-5
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696-42-4
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35590-37-5
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696-42-4
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350-04-9
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696-42-4
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402-66-4
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696-42-4
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