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Product Details of [ 17422-33-2 ]

CAS No. :17422-33-2 MDL No. :MFCD00005681
Formula : C8H6ClN Boiling Point : -
Linear Structure Formula :- InChI Key :YTYIMDRWPTUAHP-UHFFFAOYSA-N
M.W : 151.59 Pubchem ID :87111
Synonyms :
Chemical Name :6-Chloro-1H-indole

Calculated chemistry of [ 17422-33-2 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.31
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) : -5.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.74
Log Po/w (XLOGP3) : 2.68
Log Po/w (WLOGP) : 2.82
Log Po/w (MLOGP) : 2.16
Log Po/w (SILICOS-IT) : 3.22
Consensus Log Po/w : 2.52

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.13
Solubility : 0.111 mg/ml ; 0.000734 mol/l
Class : Soluble
Log S (Ali) : -2.66
Solubility : 0.329 mg/ml ; 0.00217 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.88
Solubility : 0.0199 mg/ml ; 0.000132 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.22

Safety of [ 17422-33-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 17422-33-2 ]

* 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 [ 17422-33-2 ]
  • Downstream synthetic route of [ 17422-33-2 ]

[ 17422-33-2 ] Synthesis Path-Upstream   1~54

  • 1
  • [ 17422-33-2 ]
  • [ 17808-21-8 ]
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[2] Journal of Organic Chemistry, 1990, vol. 55, # 2, p. 580 - 584
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[2] Journal of Organic Chemistry, 1990, vol. 55, # 2, p. 580 - 584
[3] Journal of Organic Chemistry, 1990, vol. 55, # 2, p. 580 - 584
[4] Heterocycles, 2012, vol. 86, # 2, p. 1015 - 1022
  • 8
  • [ 32989-56-3 ]
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Reference: [1] Chemistry of Heterocyclic Compounds, 2011, vol. 47, # 4, p. 425 - 434
  • 9
  • [ 88131-68-4 ]
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Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, # 2, p. 249 - 254
  • 10
  • [ 90001-58-4 ]
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Reference: [1] Heterocycles, 2013, vol. 87, # 1, p. 155 - 162
  • 11
  • [ 85355-58-4 ]
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Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 12, p. 2066 - 2069
  • 12
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  • [ 17422-33-2 ]
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[2] Journal of Organic Chemistry, 1990, vol. 55, # 2, p. 580 - 584
[3] Chemistry of Heterocyclic Compounds, 2011, vol. 47, # 4, p. 425 - 434
  • 13
  • [ 13617-62-4 ]
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[2] Journal of Organic Chemistry, 1983, vol. 48, # 12, p. 2066 - 2069
[3] Journal of Organic Chemistry, 1983, vol. 48, # 12, p. 2066 - 2069
  • 14
  • [ 89-63-4 ]
  • [ 17422-33-2 ]
Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 12, p. 2066 - 2069
[2] Journal of Organic Chemistry, 1983, vol. 48, # 12, p. 2066 - 2069
[3] Journal of Organic Chemistry, 1983, vol. 48, # 12, p. 2066 - 2069
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Reference: [1] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 6, p. 1625 - 1629
  • 16
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Reference: [1] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 6, p. 1625 - 1629
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  • 17
  • [ 146667-89-2 ]
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[2] Advanced Synthesis and Catalysis, 2018, vol. 360, # 8, p. 1590 - 1594
  • 18
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Reference: [1] Organic Letters, 2016, vol. 18, # 21, p. 5508 - 5511
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Reference: [1] Organic Letters, 2016, vol. 18, # 21, p. 5508 - 5511
  • 20
  • [ 27034-51-1 ]
  • [ 17422-33-2 ]
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  • 21
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  • [ 25235-85-2 ]
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[2] Tetrahedron Letters, 1989, vol. 30, # 16, p. 2129 - 2132
  • 22
  • [ 69111-49-5 ]
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Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 12, p. 2066 - 2069
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Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 12, p. 2066 - 2069
  • 24
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Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, # 2, p. 249 - 254
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Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, # 2, p. 249 - 254
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Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, # 2, p. 249 - 254
  • 27
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Reference: [1] Journal of the American Chemical Society, 1981, vol. 103, # 6, p. 1525 - 1533
  • 28
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Reference: [1] Journal of the Chemical Society, 1955, p. 3499,3502
  • 29
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Reference: [1] Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 1499 - 1501
  • 30
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Reference: [1] Heterocycles, 2013, vol. 87, # 1, p. 155 - 162
  • 31
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 18, p. 4403 - 4407
  • 32
  • [ 54664-52-7 ]
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  • 33
  • [ 75-07-0 ]
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  • 34
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Reference: [1] Journal of the Chemical Society, 1955, p. 3499,3502
  • 35
  • [ 766557-02-2 ]
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Reference: [1] Justus Liebigs Annalen der Chemie, 1955, vol. 593, p. 91,109
  • 36
  • [ 557-21-1 ]
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  • [ 15861-36-6 ]
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  • 37
  • [ 17422-33-2 ]
  • [ 75-86-5 ]
  • [ 15861-36-6 ]
Reference: [1] Organic Process Research and Development, 2016, vol. 20, # 8, p. 1540 - 1545
  • 38
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  • [ 6341-92-0 ]
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 155, p. 516 - 530
  • 39
  • [ 17422-33-2 ]
  • [ 766557-02-2 ]
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[4] Patent: WO2013/14102, 2013, A1,
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  • 40
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  • [ 107-14-2 ]
  • [ 1912-44-3 ]
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  • 41
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  • [ 1912-44-3 ]
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  • 42
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YieldReaction ConditionsOperation in experiment
100% at 20℃; for 0.333333 h; Reduction of Indoles to Indolines:; PREPARATION 142; 6-Chloro-2, 3-dihydro-lH-indole; Dissolve 6-chloro-lH-indole (2 g, 0.013 mol) in acetic acid (10 mL) under nitrogen. Add sodium cyanoborohydride (1.24 g, 1.5 eq) and stir 20 minutes at room temperature. Dilute with ethyl acetate and extract with sodium hydroxide (5 N aqueous). Dry over magnesium sulfate, filter and concentrate to give 2.35 g (116percent) crude product. MS (ES, m/z) : 154.0 (M+1).
87%
Stage #1: at 20℃; for 1 h; Inert atmosphere
Stage #2: With sodium hydroxide In water
6-chloro-2,3-dihydro-1H-indole
Under a nitrogen atmosphere 0.50 g (7.9 mmol) sodium cyanoborohydride were added batchwise to 1.0 g (6.6 mmol) 5-hydroxyindole in 5.0 mL glacial acetic acid and the mixture was stirred for 60 min at RT.
Then the reaction mixture was poured onto a 4N aqueous sodium hydroxide solution and extracted with EtOAc.
The combined organic phases were washed several times with saturated sodium hydrogen carbonate solution, dried on sodium sulphate and evaporated down.
Yield: 1.1 g (87percent of theoretical)
Rt (HPLC-MS): 1.24 min (method C)
87% at 20℃; for 3 h; Synthesis of In acetic acid (2.0 mL) solution of 6-chloro -1H- indole (200 mg, 1.3 mmol), sodium cyanoborohydride (170 mg, 2.6 mmol) was added at room temperature,and was stirred at 3 hours. It added 1 N aqueous sodium hydroxide to the reaction mixture (30 mL) at room temperature, followed by extraction with ethyl acetate (30 mL). The organic layer was dried over sodium sulfate, and concentratedIt was. The resulting concentrate was purified by silica gel column chromatography is purified by (eluent ethyl acetate / n-hexane = 25/75), 6-chloro-indoline as a colorless oilObtained (180mg, 87percent yield).
86%
Stage #1: With borane In tetrahydrofuran at 0℃; for 0.5 h;
Stage #2: With trifluoroacetic acid In tetrahydrofuran at 0℃; for 0.5 h;
Stage #3: With sodium hydroxide In tetrahydrofuran; water
Preparation 30: 6-Chloro-2,3-dihydro-1 H-indole6-Chloroindole (1.0 g, 6.6 mmol) was dissolved in a solution of borane in THF (1 M, 9.83 mmol) at 0 °C and stirred for 30 min. TFA (9.83 mL) was added dropwise and the solution stirred at 0 °C for 30 min. 6 M aqueous NaOH was added until the solution was basic (pH 1 1 ). The aqueous solution was extracted with DCM (3 x 25 mL), dried over sodium sulfate, filtered and concentrated to give the title compound (864 mg, 86percent) as a yellow oil. 1H NMR (Me-d3-OD): 6.99 (1 H, d), 6.64-6.55 (2H, m), 3.50 (2H, t), 2.95 (2H, t).
72% for 22 h; In a 250 mL round bottom flask, 12.4 grams of sodium cyanoborohydride (198 mmol, 2 eq. ) were added potion-wise over 5 minutes to a solution of 15 grams (98.9 mmol) of 6-chloroindole. After stirring for 22 hours, the mixture had become a brown solution and analysis by [HPLC] (MRH 1 method) revealed no starting material remaining and a mixture of two product peaks. The mixture was diluted with 100 [ML] of water, then made basic [WITH-200] mL of 6N sodium hydroxide. The desired product was extracted into 3 X 400 mL of methylene chloride. The extracts were then dried over anhydrous magnesium sulfate and evaporated in vacuo leaving a cloudy oil. The crude product was chromatographed over a plug of silica in 100 percent methylene chloride giving a mixed fraction [(RF=] 0.9 and 0.7), a pure product fraction [(RF= 0. 7),] and a baseline fraction (Rf = 0.0-0. 2). The pure fraction was evaporated to dryness in vacuo to yield a clear, colorless oil weighing 10.90 grams (72 percent). It was stored at [4°C] and saved for future [USE. 1H] NMR (300 MHz, DMSO-d6) 8 6.95 (d, J= 5 Hz, 1 H), 6.46 (d, [J=] 5 Hz, 2 H), 3.43 (t, [J=] 6,2 H), 2.86 (t, [J=] 6,2 H).

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  • 45
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  • [ 68-12-2 ]
  • [ 703-82-2 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: at 0℃; for 1 h;
Stage #2: at 20℃; for 5 h;
Stage #3: With sodium hydroxide In N,N-dimethyl-formamide at 100℃; for 0.166667 h;
General procedure: Oxalyl chloride (0.3 mL) was added in a drop-wise manner to cooled (ice-bath) DMF (3 mL) under stirring. The mixture was then stirred at 0 °C for 1 h. A solution of the substituted indole (4 mmol) in DMF (1.5 mL) was then added to the reaction mixture in a dropwise manner. The resulting mixture was stirred at room temperature for 5 h. A 2 N solution of sodium hydroxide (2 mL) was then added, and the mixture was heated at 100 °C for 10 min. The mixture was then cooled and extracted with ethyl acetate (3 X 50 mL). The organic layers were combined and washed with sequentially water and brine. The organics were dried (Na2SO4) and distilled to dryness to give the crude residue, which was purified by flash column chromatography using ethyl acetate/petroleum ether (3:1, v/v) as the eluent to give pure indole-3-carbaldehyde (4a-k).
85%
Stage #1: at 60℃; for 1 h;
Stage #2: With sulfuric acid In water at 50℃; for 1 h;
Example 1:
Step 1: 6-chloro-lH-indole-3-carbaldehvde
[00331] A solution of 6-Chloro-lH-indole (1.0 g, 6.59 mmol) and phosphorus oxychloride (8.56 mmol) in dimethylformamide (12 mL) was heated at 60°C for lh. Water (5 mL) andconcentrated sulfuric acid (3.95 mmol) were added to the reaction mixture then heated at 50°C for 1 h. The mixture was concentrated and the residue was diluted with water (15 mL). The aqueous phase was extracted with ethyl acetate (3 x 25 mL). The organic extracts were combined and concentrated. Purification of the residue over silica gel, 0-75percent ethyl acetate in hexanes, afforded the title compound (1.01 g, 85percent) as a tan solid. LCMS [M+H] calculated: 179.6; observed: 179.9
85%
Stage #1: at 60℃; for 1 h;
Stage #2: With sulfuric acid In water at 50℃; for 1 h;
j00370j A solution of 6-chloro-1H-indole (1.0 g, 6.59 mmol) and POC13 (8.56 mmol) in DMF (12 mL) was heated at 60°C for lh. Water (5 mL) and concentrated sulfuric acid (3.95 mmol) were added and the mixture then heated at 50°C for 1 h. The mixture was concentrated and the residue was diluted with water (15 mL). The aqueous phase was extracted with EtOAc (3 x 25 mL). The organic extracts were combined and concentrated. Purification of the residue over silica gel, 0-75percent EtOAc in hexanes, afforded the title compound (1.01 g, 85percent) as a tan solid. LCMS [M+H]: 179.9
75% at 0 - 20℃; for 3.5 h; A solution of 6-chloroindole (30 mmol) in N,N-dimethylformamide (DMF) (5 mL) was added dropwise to a solution of phosphorus oxychloride (44 mmol) in DMF (32 mL) which had been stirred for 1.5 h at 0°C. The reaction mixture was warmed to room temperature and stirred for 2 h. The solution with the precipitate formed was poured on ice and basified with solid KOH and left overnight. The precipitate was filtered and washed with a mixture of 10percent ethyl acetate in petroleum benzene several times, then left to dry to give the aldehyde. 6-Chloro-1H-indole-3-carbaldehyde (3) Synthesized according to the general procedure of Vilsmeier–Haack reaction; light brick red solid; yield 4.04 g (75percent).

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  • [ 110-18-9 ]
  • [ 703-82-2 ]
YieldReaction ConditionsOperation in experiment
72% With water; iodine; oxygen; sodium carbonate In 1,4-dioxane at 100℃; for 36 h; Schlenk technique; Sealed tube General procedure: Under air, a 20 mL of Schlenk tube equipped with a stir bar was charged with indole 1 (0.2 mmol, 1 equiv),TMEDA (75 µL, 0.5 mmol, 2.5 equiv), Na2CO3 (42.4 mg, 0.4mmol, 2.0 equiv), 1,4-dioxane (0.5 mL) and H2O (100 µL). Then I2 (101.5 mg, 0.4 mmol, 2.0 equiv) was added and the tube was sealed with a rubber plug and charged with O2. The reaction mixture was stirred at 100 °C for 36 h in oil bath. After cooling to room temperature, the resultant mixture was evaporated with EtOAc (20 mL) under reduced pressure and the residue was purified by flash column chromatography on a silica gel to give the products.
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