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8-fluoro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole synthesis
- Product Name:8-fluoro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
- CAS Number:64368-85-0
- Molecular formula:C12H13FN2
- Molecular Weight:204.24
![1-Methyl-4-piperidone](/CAS/GIF/1445-73-4.gif)
1445-73-4
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$15.00/25g
![4-Fluorophenylhydrazine hydrochloride](/CAS/GIF/823-85-8.gif)
823-85-8
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$5.00/5g
![8-fluoro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole](/CAS2/GIF/64368-85-0.gif)
64368-85-0
17 suppliers
$130.00/100mg
Yield:64368-85-0 53%
Reaction Conditions:
Stage #1: 4-fluorophenyhydrazine hydrochloridewith sulfuric acid in 1,4-dioxane at 20; for 0.0833333 h;
Stage #2: 1-Methyl-4-piperidone in 1,4-dioxane at 80; for 2 h;
Stage #3: with potassium hydroxide in water; pH=10;Product distribution / selectivity;
Steps:
18A
Example 18A [0425] Sulfuric acid (3.5 mL) was added to a solution of 4-fluorophenylhydrazine hydrochloride (2.0 g, 12.3 mmol) in dioxane (50 mL), and allowed to stir for 5 min at RT. N- methylpiperidone (1.38 g, 12 mmol) was added and the mixture was heated at 80 0C for 2 h. After completion (TLC), reaction mixture was concentrated to -20 mL under reduced pressure and basified to pH 10 using 10% aqueous KOH solution. The reaction mixture was extracted with EtOAc (3x200 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure using rotary evaporator to provide the desired compound as a brown colored solid (1 .3g, 53% yield). 1H NMR (CDCl3, free base) d (ppm) 7.90 (bs, IH), 7.18 (m, IH), 7.05 (d, IH), 6.82 (t, IH), 3.60 (s, 2H), 2.90 (m, 2H), 2.82 (m, 2H), 2.38 (s, 3H).
References:
WO2010/51501,2010,A1 Location in patent:Page/Page column 243-244
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1296771-12-4
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![8-fluoro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole](/CAS2/GIF/64368-85-0.gif)
64368-85-0
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$130.00/100mg
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1003-98-1
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![8-fluoro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole](/CAS2/GIF/64368-85-0.gif)
64368-85-0
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$130.00/100mg
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1692-25-7
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![8-fluoro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole](/CAS2/GIF/64368-85-0.gif)
64368-85-0
17 suppliers
$130.00/100mg