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[ CAS No. 52537-00-5 ] {[proInfo.proName]}

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Chemical Structure| 52537-00-5
Chemical Structure| 52537-00-5
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Product Details of [ 52537-00-5 ]

CAS No. :52537-00-5 MDL No. :MFCD07371639
Formula : C8H8ClN Boiling Point : -
Linear Structure Formula :- InChI Key :HSLNYVREDLDESE-UHFFFAOYSA-N
M.W : 153.61 Pubchem ID :258567
Synonyms :

Calculated chemistry of [ 52537-00-5 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.54
TPSA : 12.03 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) : -5.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.88
Log Po/w (XLOGP3) : 2.72
Log Po/w (WLOGP) : 1.74
Log Po/w (MLOGP) : 2.33
Log Po/w (SILICOS-IT) : 2.86
Consensus Log Po/w : 2.3

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.95
Solubility : 0.172 mg/ml ; 0.00112 mol/l
Class : Soluble
Log S (Ali) : -2.63
Solubility : 0.363 mg/ml ; 0.00236 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.6
Solubility : 0.0387 mg/ml ; 0.000252 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.33

Safety of [ 52537-00-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 52537-00-5 ]

* 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 [ 52537-00-5 ]
  • Downstream synthetic route of [ 52537-00-5 ]

[ 52537-00-5 ] Synthesis Path-Upstream   1~8

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Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 2, p. 580 - 584
[2] Advanced Synthesis and Catalysis, 2017, vol. 359, # 14, p. 2358 - 2363
[3] ACS Catalysis, 2018, vol. 8, # 2, p. 1192 - 1196
[4] Organometallics, 2018, vol. 37, # 4, p. 584 - 591
[5] Journal of Organic Chemistry, 1990, vol. 55, # 2, p. 580 - 584
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Reference: [1] Journal of the American Chemical Society, 1981, vol. 103, # 6, p. 1525 - 1533
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Reference: [1] Journal of the American Chemical Society, 1981, vol. 103, # 6, p. 1525 - 1533
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YieldReaction ConditionsOperation in experiment
79% With iodine pentoxide In dimethyl sulfoxide at 80℃; General procedure: Indoles 1 (0.5 mmol), DMSO (3mL) and I2O5 (1 mmol) were added into a flask and vigorously stirred at 80oC under air. The reaction was stopped until indoles were completely consumed as monitored by TLC analysis. After the completion of reaction, saturated Na2S2O3 solution (20 mL) was added to the mixture. The mixture was extracted with EtOAc (3×20 mL) and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated on a rotary evaporator. Then, the crude product was purified by column chromatography on silica gel using ethyl acetate and petroleum ether as the eluent to give the products 2.
Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 18, p. 1747 - 1750
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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).

Reference: [1] Patent: WO2003/76398, 2003, A2, . Location in patent: Page/Page column 41
[2] Patent: US2011/21500, 2011, A1, . Location in patent: Page/Page column 49
[3] Patent: JP2015/193573, 2015, A, . Location in patent: Paragraph 0043
[4] Patent: WO2012/143726, 2012, A1, . Location in patent: Page/Page column 129
[5] Journal of Medicinal Chemistry, 2015, vol. 58, # 16, p. 6574 - 6588
[6] Patent: WO2004/18414, 2004, A2, . Location in patent: Page 92
[7] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 21, p. 3105 - 3109
[8] Patent: US2004/266843, 2004, A1, . Location in patent: Page 22
[9] Journal of Medicinal Chemistry, 2011, vol. 54, # 1, p. 166 - 178
[10] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 5, p. 373 - 377
[11] Chemistry - A European Journal, 2014, vol. 20, # 1, p. 58 - 63
[12] Journal of Organic Chemistry, 2016, vol. 81, # 2, p. 396 - 403
[13] Journal of the American Chemical Society, 2016, vol. 138, # 37, p. 12234 - 12242
[14] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 2425 - 2437
[15] Organic and Biomolecular Chemistry, 2018, vol. 16, # 32, p. 5889 - 5898
[16] Organic and Biomolecular Chemistry, 2018, vol. 16, # 21, p. 3889 - 3892
[17] Patent: US2008/81810, 2008, A1, . Location in patent: Page/Page column 67
  • 6
  • [ 76653-03-7 ]
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Reference: [1] Journal of the American Chemical Society, 1981, vol. 103, # 6, p. 1525 - 1533
  • 7
  • [ 54664-52-7 ]
  • [ 1073-67-2 ]
  • [ 17422-33-2 ]
  • [ 52537-00-5 ]
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Reference: [1] Journal of the American Chemical Society, 1981, vol. 103, # 6, p. 1525 - 1533
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Reference: [1] Journal of the American Chemical Society, 1981, vol. 103, # 6, p. 1525 - 1533
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