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[ CAS No. 2380-94-1 ] {[proInfo.proName]}

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Chemical Structure| 2380-94-1
Chemical Structure| 2380-94-1
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Quality Control of [ 2380-94-1 ]

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Product Details of [ 2380-94-1 ]

CAS No. :2380-94-1 MDL No. :MFCD00005667
Formula : C8H7NO Boiling Point : -
Linear Structure Formula :- InChI Key :NLMQHXUGJIAKTH-UHFFFAOYSA-N
M.W : 133.15 Pubchem ID :75421
Synonyms :

Calculated chemistry of [ 2380-94-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 40.32
TPSA : 36.02 ?2

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) : -5.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.22
Log Po/w (XLOGP3) : 1.69
Log Po/w (WLOGP) : 1.87
Log Po/w (MLOGP) : 0.91
Log Po/w (SILICOS-IT) : 2.1
Consensus Log Po/w : 1.56

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.4
Solubility : 0.535 mg/ml ; 0.00402 mol/l
Class : Soluble
Log S (Ali) : -2.06
Solubility : 1.16 mg/ml ; 0.00868 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.67
Solubility : 0.282 mg/ml ; 0.00212 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.15

Safety of [ 2380-94-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2380-94-1 ]

* 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 [ 2380-94-1 ]

[ 2380-94-1 ] Synthesis Path-Downstream   1~9

  • 1
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  • 2
  • [ 85926-99-4 ]
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  • 3
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  • [ 108-24-7 ]
  • [ 5585-96-6 ]
YieldReaction ConditionsOperation in experiment
99.2% With pyridine; In dichloromethane; at 0 - 25℃;Inert atmosphere; Large scale; 4-hydroxyindole (1eq. limiting reagent) was charged to a vessel under N2 followed by DCM (dichloromethane; 6 vol based on 4-hydroxyindole charge). The reaction was cooled to 0-5C and pyridine added (1.2 eq) dropwise at 0-5C. Acetic anhydride (1.1 eq) was added dropwise at 0-5C and the reaction warmed to 20-25C for 1 - 1.5 hrs and stirred at 20-25C for a further 3 hours. The reaction was sampled and analysed for completion. The reaction was then washed three times with 20% aqueous citric acid solution (3 x 3 vol based on 4-hydroxyindole charge) and once with sat. NaHCC-3 (3 vol based on 4-hydroxyindole charge). The DCM solution was dried over MgSC and filtered and the DCM layer concentrated to half volume by distillation. Heptane (6 vol based on 4-hydroxyindole charge) was added and further DC was removed by distillation until full precipitation of the Stage 1 had occurred. The reaction was cooled to 15-25C and the solids collected by filtration, washing with heptane (1 vol based on 4-hydroxyindole charge) dried under vacuum overnight at 60C.
  • 4
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  • [ 889675-05-2 ]
  • 5
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  • [ 68-12-2 ]
  • [ 81779-27-3 ]
YieldReaction ConditionsOperation in experiment
82% EXAMPLE 1 OF REFERENCE 4-Hydroxyindole-3-carbaldehyde (1-1) (R7=R11=H) phosphorous oxychloride 7.35 ml was added dropwise to dry dimethylformamide 15 ml under cooling in ice-methanol bath and the mixture was stirred for 15 min.Then, a solution of the 4-hydroxyindole 5.0 g in dry dimethylformamide 10 ml was added dropwise to the mixture under cooling in ice and the mixture was stirred for 2 h at room temperature.water was added under cooling in ice to the mixture, which was made alkaline with a 30% aqueous sodium hydroxide solution and was stirred for 15 min.Then, the mixture was acidified to PH 4 with 5N-HCl and the precipitate was collected by filtration, washed with water and dried to give the titled compound 4.99 g as crude crystalline materials.Yield 82%.Crude crystalline materials are recrystallized from methanol to give yellow crystals m.p. 190-193 C. 1H-NMR(DMSO-d6): 6.54 (1H, dd, J=8.1, 0.9 Hz), 6.95 (1H, dd, J=8.1, 0.9 Hz), 7.13 (1H, t, J=8.1 Hz), 8.37 (1H, s), 9.64 (1H, s), 10.54 (1H, br s), 12.35 (1H, br s).
  • 6
  • [ 2380-94-1 ]
  • [ 85926-99-4 ]
YieldReaction ConditionsOperation in experiment
100% Synthesis of CDNI-GAB A.; [0068] Synthesis of compound 2b.; 4-Acetoxy-l-acetylindoline. A solution of 4-hydroxyindole (6.66 g, 50 mmol) in acetic acid (250 mL) was treated with NaBH3CN (9.42 g, 150 mmol) over 0.5 h, keeping the temperature at <15 C. The mixture was then stirred at room temperature for 1 h and water (5 mL) was added and the solvent evaporated. The residue was dissolved in EtOAc (150 mL) and washed with saturated aq. NaHCO3 and brine, dried and evaporated to give 4- hydroxyindoline as pale crystals (6.76 g. 100%); IH NMR (δ, CDCl3 DMSO-J6): 6.82 (IH, t, J= 8 Hz), 6.20 (IH, d, J= 8 Hz), 6.16 (IH, d, J= 8 Hz), 3.52 (2H, t, J= 8 Hz) and 2.90 (2H, d, J= 8 Hz). The crude indoline was dissolved in a mixture of acetic acid (50 mL) and acetic anhydride (50 mL) and heated under reflux for 1 h. The solution was diluted with water (10 mL) and the solvents evaporated. The residue was dissolved in EtOAc (150 mL) and washed with saturated aq. NaHCO3 and brine, dried and evaporated to give 4-acetoxy-l- acetylindoline as pale crystals (9.01 g, 82%), NMR (δ, 90 MHz): 8.07 (IH, d, J= 8 Hz), 7.19 (IH, t, J= 8 Hz), 6.72 (IH, d, J= 8 Hz), 4.05 (2H, t, J= 8 Hz), 3.03 (2H, t, J= 8 Hz) 2.28 (3H, s) and 2.19 (3H, s).
100% With sodium cyanotrihydridoborate; In glacial acetic acid; at 15 - 20℃; for 1.5h; A solution of 4-hydroxyindole 26 (6.66 g, 50 mmol) in acetic acid (250 mL) was treated with NaBH3CN (9.42 g, 150 mmol) over 0.5 h, keeping the temperature at-15oC. The mixture was stirred at room temperature for 1 h and water (5 mL) was added and the solvent evaporated. The residue was dissolved in EtOAc (150 mL) and washed with saturated aq. NAHC03 and brine, dried and evaporated to give 4- hydroxyindoline as pale crystals (6. 76 g. 100%) ; 1H NMR: (90 MHz, CDC13 + DMSO-d6) # 6. 82 (1H, t, J = 8 Hz), 6.20 (1H, d, J = 8 Hz), 6.16 (1H, d, J = 8 Hz), 3.52 (2H, t, J = 8 Hz) and 2.90 (2H, d, J = 8 Hz).
99% With sodium cyanotrihydridoborate; In glacial acetic acid; at 15 - 20℃; A solution of 4-hydroxyindole (0.16 g; 1.2 mmol) in AcOH (6 ml) was treated with NaBH3CN (0.23 g; 3.6 mmol), at rate keeping the temperature below 150C. The mixture was then stirred for 1 h at room temperature and H2O (0.4 ml) was added and solvents removed in vacuo. The residue was diluted to 15 ml with EtOAc, washed with 5% NaHCO3, brine, dried over anhydrous MgSO4, filtered and filtrate evaporated under reduced pressure to give the title compound (0.16 g; 99%) as creamy solid. 1 H-NMR (CDCI3 ) 2.93 (tr, 2H, J = 8.4 Hz); 3.58 (tr, 2H, J = 8.4 Hz); 3.74 (broad S, 2H); 6.17 (d, 1 H, J = 8 Hz); 6.26 (d, 1 H, J = 7.72 Hz); 6.88 (tr, 1 H, J = 7.85 Hz).
92% With sodium cyanotrihydridoborate; glacial acetic acid; at 0 - 20℃; for 1h; Take 2.12 g of 4-hydroxyindole into a 100 mL flask, add 30 mL of glacial acetic acid, and stir under ice bath. Weigh 1.51 g of sodium cyanoborohydride into a small Erlenmeyer flask and stopper. Then add sodium cyanoborohydride to a small amount of batchwise mixture. After stirring for 1 hour at room temperature, add 5mL deionized water and stir for 10min, remove acetic acid under reduced pressure, pour into 100mL:200mL ethyl acetate and water mixture, add 1.8g sodium bicarbonate, stir until no bubbles are generated, extract and separate The organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was decompressed to remove the solvent to obtain 1.98 g of solid, with a yield of 92%. The hydrogen spectrum data of the NMR spectrum are as follows:
66.99% With sodium cyanotrihydridoborate; glacial acetic acid; at 0 - 20℃; for 0.5h; At room temperature, 1H-indol-4-ol (10 g) was dissolved in AcOH (30 ml), and after cooling in an ice bath, sodium cyanoborohydride (11.80 g) was added in batches, and the temperature was controlled below 15C for 0.5 reaction h. Ice water was added to quench the reaction, saturated aqueous sodium carbonate solution was adjusted to neutral pH, extracted twice with EA (300ml*2), the organic phases were combined, washed with saturated brine, and concentrated. The concentrate was separated and purified by silica gel column (DCM:MeOH=99:1-30:1) to obtain white-green product 1-1 (6.8 g, yield 66.99%).
59% With sodium cyanotrihydridoborate; In glacial acetic acid; at 0 - 20℃; for 3h;Inert atmosphere; General procedure: NaBH(CN)3 (1.4 g, 22.60 mmol) was added slowly to a solution of 8 (1.0 g, 7.51 mmol) in AcOH (20 mL) at 0, and then the mixture was stirred for 3 h at room temperature under N2 atmosphere. The resulting reaction mixture was quenched with saturated NH4Cl solution (3 mL) and concentrated under reduced pressure to give the residue, which was redissolved in EtOAc (50 mL), and washed with saturated NaHCO3 (50 mL), brine (50 mL), dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography eluting with petroleum ether/ethyl acetate (5:1-3:1-2:1, v/v) to provide the intermediate 9 (0.61 g, 60% yield) as a brown solid.

  • 7
  • [ 2380-94-1 ]
  • [ 81779-27-3 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; trichlorophosphate; In N-methyl-acetamide; water; 4-Hydroxyindole-3-carbaldehyde(1-1) (R7=R11=H) Phosphorous oxychloride 7.35 ml was added dropwise to dry dimethylformamide 15 ml under cooling in ice-methanol bath and the mixture was stirred for 15 min. Then, a solution of the 4-hydroxyindole 5.0 g in dry dimethylformamide 10 ml was added dropwise to the mixture under cooling in ice and the mixture was stirred for 2 h at room temperature. Water was added under cooling in ice to the mixture, which was made alkaline with a 30% aqueous sodium hydroxide solution and was stirred for 15 min. Then, the mixture was acidified to pH 4 with 5N-HCl and the precipitate was collected by filtration, washed with water and dried to give the titled compound 4.99 g as crude crystalline materials. Yield 82%. Crude crystalline materials are recrystallized from methanol to give yellow crystals m.p. 190-193 ?C. 1H-NMR(DMSO-d6): 6.54 (1H, dd, J = 8.1, 0.9 Hz), 6.95 (1H, dd, J = 8.1, 0.9 Hz), 7.13 (1H, t, J = 8.1 Hz), 8.37 (1H, s), 9.64 (1H, s), 10.54 (1H, br s), 12.35 (1H, br s).
  • 8
  • [ 2380-94-1 ]
  • [ 60827-45-4 ]
  • [ 80183-74-0 ]
YieldReaction ConditionsOperation in experiment
80% General procedure: (S)-3-(4-Indolyloxy)-propane-1,2-diol, (S)-4 was preparedfrom 250 mg (1.9 mmol) 4-hydroxyindole and (S)-3-chloropropane-1,2-diol (0.243 g, 2.2 mmol), as described above for rac-4.The yield was 310 mg (80%); mp 122 C (Et2O-MeCN, 3:1 v/v);a20D = +5.2 (c 1.49, MeOH); 96% ee {lit. [9]: mp 119-120 C;a20D = +5.1 (c 1.47, MeOH)}. 1H and 13C NMR spectra were identicalwith that cited above for rac-4
  • 9
  • [ 2380-94-1 ]
  • [ 1196155-38-0 ]
  • 2-((1H-indol-4-yl)oxy)-6-(trifluoromethyl)isonicotinonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% With chloro-trimethyl-silane; potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 150℃; for 0.75h;Microwave irradiation; To a stirred solution of lH-indol-4-ol 1 (500 mg, 3.76 mmol) in N-methyl-2- pyrrolidone (12.5 mL) were added 2-chloro-6-(trifluoromethyl) isonicotinonitrile (774 mg, 3.76 mmol), K2C03 (1.04 g, 7.52 mmol) and TMS-C1 (0.5 mL, 3.76 mmol). The reaction mixture was heated to 150 °C in a microwave synthesizer for 45 min. The reaction mixture was quenched with water (40 mL) and extracted with Et20 (2 x 50 mL). The combined organic extracts were washed with brine (20 mL), dried (Na2S04), filtered and concentrated under reduced pressure. The crude was purified (silica gel; eluting 4percent EtOAc/ hexanes) to afford compound 2 (180 mg, 16percent) as an off-white solid.1H MR (400 MHz, DMSO-i): delta 11.37 (br s, 1H), 8.16 (d, 7= 0.7 Hz, 1H), 7.90 (s, 1H), 7.37-7.32 (m, 2H), 7.14 (t, J= 7.9 Hz, 1H), 6.86 (dd, J= 7.6, 0.6 Hz, 1H), 6.14-6.13 (m, 1H); LC-MS (ESI): 72.74percent; m/z 303.9 (M + H+).
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