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[ CAS No. 40311-13-5 ] {[proInfo.proName]}

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Product Details of [ 40311-13-5 ]

CAS No. :40311-13-5 MDL No. :MFCD09027714
Formula : C9H8FN Boiling Point : -
Linear Structure Formula :- InChI Key :DQDVUUGKFGUZCF-UHFFFAOYSA-N
M.W : 149.17 Pubchem ID :9942185
Synonyms :

Calculated chemistry of [ 40311-13-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.11
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.22
TPSA : 15.79 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.4 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.87
Log Po/w (XLOGP3) : 2.55
Log Po/w (WLOGP) : 3.04
Log Po/w (MLOGP) : 2.31
Log Po/w (SILICOS-IT) : 3.41
Consensus Log Po/w : 2.64

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.98
Solubility : 0.157 mg/ml ; 0.00105 mol/l
Class : Soluble
Log S (Ali) : -2.53
Solubility : 0.441 mg/ml ; 0.00296 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.93
Solubility : 0.0175 mg/ml ; 0.000117 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.51

Safety of [ 40311-13-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302+H312+H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 40311-13-5 ]

* 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.

  • Upstream synthesis route of [ 40311-13-5 ]
  • Downstream synthetic route of [ 40311-13-5 ]

[ 40311-13-5 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 39616-99-4 ]
  • [ 40311-13-5 ]
YieldReaction ConditionsOperation in experiment
97% With [2,2]bipyridinyl; carbon monoxide In toluene EXAMPLE 5
Synthesis of 6-fluoro-2-methylindole
In a stainless steel autoclave having an internal volume of 100 mL, 1.0 g (5.1 mmol) of 4-fluoro-2-nitrophenylacetone, 130 mg (4 mol percent) of trirutheniumdodecacarbonyl, 397 mg of 2,2'-bipyridyl and 40 g of toluene were placed under nitrogen atmosphere, and the reaction was conducted similarly to Example 4.
After the reaction, the reaction solution was subjected to quantitative analysis with liquid chromatography.
As a result of it, it was confirmed that the conversion rate of 4-fluoro-2-nitrophenylacetone was 100percent and 0.65 g (yield 97.0percent) of 6-fluoro-2-methylindole was formed.
95% With carbon monoxide In toluene at 120℃; for 9 h; EXAMPLE 1 Synthesis of 6-fluoro-2-methylindole In a stainless steel autoclave having an internal volume of 100 mL, 1.0 g (5.1 mmol) of 4-fluoro-2-nitrophenylacetone, 72 mg (4 mol percent) of cyclopentadienyidicarbonyliron (dimer) and 40 g of toluene were placed under nitrogen atmosphere. After the atmosphere inside of the reactor was substituted by nitrogen gas (10 kgf/cm2) three times, carbon monoxide gas was injected (50 kgf/cm2), and the resulting mixture was reacted at a temperature of 120 C. for 5 hours. After cooling, the reaction solution was subjected to quantitative analysis with liquid chromatography. As a result of it, it was confirmed that 4-fluoro-2-nitrophenylacetone was completely disappeared and 0.64 g (yield 95.0percent) of 6-fluoro-2-methylindole was formed.
91% With carbon monoxide; tin(ll) chloride In 1,4-dioxane at 120℃; for 9 h; EXAMPLE 2 Synthesis of 6-fluoro-2-methylindole In a stainless steel autoclave having an internal volume of 100 mL, 1.0 g (5.1 mmol) of 4-fluoro-2-nitrophenylacetone, 178 mg (5 mol percent) of dichlorobis(triphenylphosphine)palladium, 0.48 g tin (II) chloride and 40 g of 1,4-dioxane were placed under nitrogen atmosphere. After the atmosphere inside of the reactor was substituted by nitrogen gas (10 kgf/cm2) three times, carbon monoxide gas was injected (20 kgf/cm2), and the resulting mixture was reacted at a temperature of 120 C. for 9 hours. After cooling, the reaction solution was subjected to quantitative analysis with liquid chromatography. As a result of it, it was confirmed that 4-fluoro-2-nitrophenylacetone was consumed by 98percent and 0.61 g (yield 91.0percent) of 6-fluoro-2-methylindole was formed.
79% With carbon monoxide In toluene at 180℃; for 4 h; EXAMPLE 4 Synthesis of 6-fluoro-2-methylindole In a stainless steel autoclave having an internal volume of 100 mL, 1.0 g (5.1 mmol) of 4-fluoro-2-nitrophenylacetone, 130 mg (4 mol percent) of trirutheniumdodecacarbonyl and 40 g of toluene were placed under nitrogen atmosphere. After the atmosphere inside of the reactor was substituted by nitrogen gas (10 kgf/cm2) three times, carbon monoxide gas was injected (50 kgf/cm2), and the resulting mixture was reacted at a temperature of 180 C. for 4 hours. After cooling, the reaction solution was subjected to quantitative analysis with liquid chromatography. As a result of it, it was confirmed that the conversion rate of 4-fluoro-2-nitrophenylacetone was 91 percent and 0.53 g (yield 79.0percent) of 6-fluoro-2-methylindole was formed.
71% With acetic acid; zinc In ethanol at 80℃; for 4 h; 3e (0.5mmol, 99 mg), zinc powder (3.0mmol, 196 mg), acetic acid (6.0mmol, 360 mg) put into the 25 ml in the reaction tube, and adding ethanol to 2 ml, 80 °C is stirred under the condition 4h. After cooling to room temperature the temperature of the reaction system by adding 25 ml water, add 25 ml ethyl acetate extraction, grass-roots takes has saturated salt water for washing, for Na2 SO4 Drying, then adding a small amount of silica gel turns on lathe the main column chromatography, to obtain white solid 4e (71percent).
44% With carbon monoxide; tin(ll) chloride In 1,4-dioxane at 120℃; for 8 h; EXAMPLE 7 Synthesis of 6-fluoro-2-methylindole In a stainless steel autoclave having an internal volume of 100 mL, 1.0 g (5.1 mmol) of 4-fluoro-2-nitrophenylacetone, 102.5 mg (4 mol percent) of dichlorobis(triphenylphosphine)platinum, 0.48 g of tin(II) chloride and 30 g of 1,4-dioxane were placed under nitrogen atmosphere. After the atmosphere inside of the reactor was substituted by nitrogen gas (10 kgf/cm2) three times, carbon monoxide gas was injected (50 kgf/cm2), and the resulting mixture was reacted at a temperature of 120 C. for 8 hours. After cooling, the reaction solution was subjected to quantitative analysis with liquid chromatography. As a result of it, it was confirmed that the conversion rate of 4-fluoro-2-nitrophenylacetone was 92percent and 0.29 g (yield 44.0percent) of 6-fluoro-2-methylindole was formed.
13% With titanium(III) chloride; ammonium acetate In water; acetone for 1 h; C: 6-Fluoro-2-methyl-lH-indoleTo a solution of l-(4-fluoro-2-nitrophenyl)-2-propanone (200mg 1.0 mmol) in acetone (3 mL) was added aqueous NH4OAc (IM, 30 mL, 30 mmol). To the mixture was added TiCb (1 M, 7 mL, 7 mmol). The mixture was stirred for 1 hour, then extracted with EtOAc. The organic layer was dried and concentrated in vacuo. The residue was purified by normal phase silica gel chromatography to afford the desired product (20 mg, 0.13 mmol, 13 percent yield).
10% With carbon monoxide; triphenylphosphine; tin(ll) chloride In 1,4-dioxane at 120℃; for 4 h; EXAMPLE 8 Synthesis of 6-fluoro-2-methylindole In a stainless steel autoclave having an internal volume of 100 mL, 1.0 g (5.1 mmol) of 4-fluoro-2-nitrophenylacetone, 0.05 g of 5percent palladium supported on active carbon [manufactured by N.E. CHEMCAT CORPORATION (50percent water-containing product)], 0.48 g of tin (II) chloride, 0.20 g of triphenylphosphine and 40 g of 1,4-dioxane were placed under nitrogen atmosphere. After the atmosphere inside of the reactor was substituted by nitrogen gas (10 kgf/cm2) three times, carbon monoxide gas was injected (20 kgf/cm2), and the resulting mixture was reacted at a temperature of 120 C. for 4 hours. After cooling, the reaction solution was subjected to quantitative analysis with liquid chromatography. As a result of it, it was confirmed that the conversion rate of 4-fluoro-2-nitrophenylacetone was 33percent and 0.07 g (yield 10.0percent) of 6-fluoro-2-methylindole was formed.

Reference: [1] Patent: US2007/83053, 2007, A1, . Location in patent: Page/Page column 7
[2] Patent: US2007/83053, 2007, A1, . Location in patent: Page/Page column 6
[3] Patent: US2007/83053, 2007, A1, . Location in patent: Page/Page column 6
[4] Patent: US2007/83053, 2007, A1, . Location in patent: Page/Page column 6
[5] Organic and Biomolecular Chemistry, 2016, vol. 14, # 44, p. 10511 - 10515
[6] Patent: US2007/83053, 2007, A1, . Location in patent: Page/Page column 6
[7] Patent: CN106631968, 2017, A, . Location in patent: Paragraph 0053-0056; 0058
[8] Patent: US2007/83053, 2007, A1, . Location in patent: Page/Page column 7
[9] Patent: WO2009/49113, 2009, A1, . Location in patent: Page/Page column 22
[10] Patent: US2007/83053, 2007, A1, . Location in patent: Page/Page column 7
[11] Patent: WO2006/57354, 2006, A1, . Location in patent: Page/Page column 18-19; 21
  • 2
  • [ 39616-99-4 ]
  • [ 40311-13-5 ]
YieldReaction ConditionsOperation in experiment
70% With hydrogen In butan-1-ol at 100℃; for 24 h; COMPARATIVE EXAMPLE 2 Synthesis of 6-fluoro-2-methylindole In a reaction flask the atmosphere inside of which was substituted by nitrogen, 1.00 g (5.1 mmol) of 4-fluoro-2-nitrophenylacetone, 10 g of 1-butanol and 0.05 g of 5percent palladium supported on active carbon [manufactured by N.E. CHEMCAT CORPORATION (50percent water-containing product)] were placed, hydrogen gas was supplied therein at ordinary pressure and 100 C., and the resulting mixture was reacted for 24 hours. After confirming the disappearance of 4-fluoro-2-nitrophenylacetone with liquid chromatography, the atmosphere was substituted by nitrogen, and the catalyst was filtered off through celite. The reaction solution was subjected to quantitative analysis with liquid chromatography, and as a result of it, it was confirmed that 0.53 g (yield 70percent) of 6-fluoro-2-methylindole was formed, and further 6-fluoro-1-hydroxy-2-methylindole and 6-fluoro-2-methylindoline were formed in a yield of 3percent and 25percent, respectively.
17% With hydrogen In 2-ethoxy-ethanol at 20℃; for 24 h; COMPARATIVE EXAMPLE 1 Synthesis of 6-fluoro-2-methylindole In a reaction flask the atmosphere inside of which was substituted by nitrogen, 1.00 g (5.1 mmol) of 4-fluoro-2-nitrophenylacetone, 10 g of 2-ethoxyetanol and 0.05 g of 5percent palladium supported on active carbon [manufactured by N.E. CHEMCAT CORPORATION (50percent water-containing product)] were placed, hydrogen gas was supplied therein at ordinary pressure and 20 C., and the resulting mixture was reacted for 24 hours. After confirming the disappearance of 4-fluoro-2-nitrophenylacetone with liquid chromatography, the atmosphere was substituted by nitrogen, and the catalyst was filtered off through celite. The reaction solution was subjected to quantitative analysis with liquid chromatography, and as a result of it, it was confirmed that 0.13 g (yield 17percent) of 6-fluoro-2-methylindole was formed, and further 6-fluoro-1-hydroxy-2-methylindole and 6-fluoro-2-methylindoline were formed in a yield of 55percent and 11percent, respectively.
Reference: [1] Patent: US2007/83053, 2007, A1, . Location in patent: Page/Page column 9
[2] Patent: US2007/83053, 2007, A1, . Location in patent: Page/Page column 9
  • 3
  • [ 1383976-65-5 ]
  • [ 40311-13-5 ]
YieldReaction ConditionsOperation in experiment
1.1 g With copper(l) iodide In N,N-dimethyl-formamide for 1 h; Reflux Step 2a:6-Difluoro-2-methylindole 43 mg of copper(I) iodide are added to a solution of 1.7 g of 5-difluoro-2-prop-1-ynylphenylamine in 50 ml of DMF. The reaction medium is refluxed for one hour.After cooling, the reaction medium is filtered. The filtrate is concentrated under reduced pressure. The crude residue obtained is purified on a silica column, eluent: 90/10 cyclohexane/ethyl acetate, so as to give 1.1 g of 6-fluoro-2-methylindole, the characteristics of which are the following:Mass spectrometry: method ARetention time Tr (min)=0.89; [M+H]+: m/z 150
Reference: [1] Patent: US2013/274253, 2013, A1, . Location in patent: Paragraph 1393-1398
  • 4
  • [ 39616-99-4 ]
  • [ 66-71-7 ]
  • [ 40311-13-5 ]
Reference: [1] Patent: US2007/83053, 2007, A1, . Location in patent: Page/Page column 7
  • 5
  • [ 446-09-3 ]
  • [ 40311-13-5 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 44, p. 10511 - 10515
  • 6
  • [ 606092-05-1 ]
  • [ 40311-13-5 ]
  • [ 1643-19-2 ]
  • [ 348635-87-0 ]
YieldReaction ConditionsOperation in experiment
91.2% With sodium hydroxide In water; toluene Example 8
Production of 1-(N,N-dimethylsulfamoyl)-3-(3-bromo-6-fluoro-2-methylindol-1-yl) sulfonyl-1,2,4-triazole
In the solution of 3-bromo-6-fluoro-2-methylindole in toluene prepared from 7.00 g (0.0469 mol) of 6-fluoro-2-methylindole in the preceding step, 14.2 g (0.0516 mol) of 3-chlorosuffonyl-1-(N,N-dimethylsulfamoyl)-3-chlorosulfonyl-1,2,4-triazole in 85.1 g of toluene and 0.151 g (0.000469 mol) of tetrabutyl ammonium bromide were added, and 5.99 g (0.0704 mol) of 48percent sodium hydroxide was added dropwise at -5 to 0°C over 4 hours, and stirred at -5 to 0°C further for 3 hours.
After the completion of the reaction, 32 g of water was added, the temperature was raised to 40°C, the resulting mixture was subjected to phase-separation, and then washed with 32 g of water two times to obtain a solution of 20.0 g (yield 91.2percent) of 1-(N,N-dimethylsulfamoyl)-3-(3-bromo-e-fluoro-2-methylindol-1-yl) sulfonyl-1,2,4-triazole being an aimed product in toluene.
Reference: [1] Patent: EP1829872, 2007, A1,
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