![](/CAS/GIF/73139-85-2.gif)
5-FLUOROINDOLE-3-ACETONITRILE synthesis
- Product Name:5-FLUOROINDOLE-3-ACETONITRILE
- CAS Number:73139-85-2
- Molecular formula:C10H7FN2
- Molecular Weight:174.17
![5-Fluoroindole](/CAS/GIF/399-52-0.gif)
399-52-0
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![Formaldehyde](/CAS/GIF/50-00-0.gif)
50-00-0
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![Trimethylsilyl cyanide](/CAS/GIF/7677-24-9.gif)
7677-24-9
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$19.00/5g
![5-FLUOROINDOLE-3-ACETONITRILE](/CAS/GIF/73139-85-2.gif)
73139-85-2
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Yield:73139-85-2 61%
Reaction Conditions:
Stage #1: 5-fluoro-1H-indole;formaldehydwith acetic acid;dimethyl amine in water at 20; for 6 h;
Stage #2: with 3-(Dimethylaminomethyl)indole;methyl iodide in dichloromethane;toluene at 20; for 12 h;
Stage #3: trimethylsilyl cyanidewith tetrabutyl ammonium fluoride in tetrahydrofuran at 20; for 4 h;Inert atmosphere;
Steps:
25.1 1) Preparation of(5-fluoro-1 H-indol-3-yl)-acetonitrile
To a solution of 5-fluoroindole (0.9 g, 6.8 mmol, 1.0 eq.) inhydroxide. The mixture was extracted with dichioromethane and then, the organic layer was dried over MgSO4 and par- 45 tially evaporated. To the solution gramine in dichioromethane (20 mL) were added, under an argon atmosphere, anhydrous toluene (40 mL) and methyl iodide (824 pL, 13.2 mmol, 2.0 eq.). The mixture was stirred at room temperature for 12 hours and then, concentrated under reduced pressure. To the 50 residue taken up in anhydrous THF (60 mL) were added, under an argon atmosphere, TMSCN (1.25 mL, 9.9 mmol, 1.5 eq.) and TI3AF (19.9 mL, 1M, 19.9 mmol, 3.0 eq.). The mixture was stirred at room temperature for 4 hours and then, concentrated under reduced pressure. The crude was taken up 55 in ethyl acetate and the organic layer was washed with aqueous bicarbonate solution and then dried over MgSO4. The solvent was removed under reduced pressure, and the residue purified by silica gel flash-column chromatography (eluent:heptane/CH2C12, 80:20 to 40:60) to afford (S-fluoro-1H-in- 60 dol-3-yl)-acetonitrile as beige oil (0.70 g, 61%).a mixture of acetic acid (2 mL) and water (1 mL) were added,at 0° C., formaldehyde (720 pL, 37% in H20, 8.9 mmol, 1.3 40eq) and dimethylamine (1.23 mL, 40% in H20, 10.9 mmol,1.7 eq). The mixture was stirred at room temperature for 6hours and then, quenched with ice and S M aqueous sodium
References:
US9212138,2015,B2 Location in patent:Page/Page column 52; 53
![5-Fluoroindole](/CAS/GIF/399-52-0.gif)
399-52-0
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![Gramine](/CAS/GIF/87-52-5.gif)
87-52-5
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![Iodomethane](/CAS/GIF/74-88-4.gif)
74-88-4
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![5-FLUOROINDOLE-3-ACETONITRILE](/CAS/GIF/73139-85-2.gif)
73139-85-2
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![5-Fluoroindole](/CAS/GIF/399-52-0.gif)
399-52-0
361 suppliers
$10.00/1g
![5-FLUOROINDOLE-3-ACETONITRILE](/CAS/GIF/73139-85-2.gif)
73139-85-2
32 suppliers
inquiry