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[ CAS No. 25235-85-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 25235-85-2
Chemical Structure| 25235-85-2
Chemical Structure| 25235-85-2
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Product Citations

Shriver, James A. ; Kaller, Kaylie S. ; Kinsey, Ally L. , et al. DOI: PubMed ID:

Abstract: The spontaneous conversion of 3-indoxyl to indigo was a well-established process used to produce indigo dyes. It was recently shown that some indoles, when reacted with molybdenum hexacarbonyl and cumyl peroxide, proceed through an indoxyl intermediate to produce significant amounts of indirubin through a competing mechanism. Modulation of this system to lower temperatures allows for careful tuning, leading to selective production of indirubins in a general process. A systematic assay of indoles show that electron deficient indoles work well when substituted at the 5 and 7 positions. In contrast, 6-substituted electron rich indoles give the best results whereas halogeno indoles work well in all cases. This process shows broad functional group tolerance for generally reactive carbonyl-containing compounds such as aldehydes and carboxylic acids.

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Product Details of [ 25235-85-2 ]

CAS No. :25235-85-2 MDL No. :MFCD00005665
Formula : C8H6ClN Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 151.59 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 25235-85-2 ]      Expand+

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) : 1.7
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 : 2.51

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 [ 25235-85-2 ]

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 [ 25235-85-2 ]

* 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 [ 25235-85-2 ]
  • Downstream synthetic route of [ 25235-85-2 ]

[ 25235-85-2 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 121-73-3 ]
  • [ 1826-67-1 ]
  • [ 17422-33-2 ]
  • [ 25235-85-2 ]
  • [ 108-42-9 ]
Reference: [1] Tetrahedron Letters, 1989, vol. 30, # 16, p. 2129 - 2132
[2] Tetrahedron Letters, 1989, vol. 30, # 16, p. 2129 - 2132
  • 2
  • [ 25235-85-2 ]
  • [ 68-12-2 ]
  • [ 876-72-2 ]
YieldReaction ConditionsOperation in experiment
44% at 10 - 37℃; for 0.75 h; To a stirring DMF (10.63 mL) was added dropwise POC13 (3.55 mL) at 10-20 °C followed by addition of a solution of SM1 (2 g,13.19 mmol) at 20-30 °C. Thereaction mixture was stirred at 35-37 °C for 45 minutes and finally poured into stirred ice(28 g) and water (21 mL). Sodium hydroxide (6.86 g) in water (36 mL) was added at 20-30°C and made the solution pH=8. The mixture was boiled for 5 minutes and cooled to roomtemperature, extracted with EtOAc, washed with brine. Combined organic extracts were dried over anhydrous Na2504 and concentrated under reduced pressure to obtain crude product, which was purified by silica gel column chromatography eluting with 60percent PE/EtOAc to afford compound 1 (1.037 g, 44percent) as an off-white solid. LC-MS: m/z =180[(M+1)].
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9179 - 9195
[2] Organic Letters, 2013, vol. 15, # 17, p. 4330 - 4333
[3] Patent: WO2016/44777, 2016, A1, . Location in patent: Page/Page column 72; 73
[4] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 6, p. 1793 - 1798
[5] Organic and Biomolecular Chemistry, 2018, vol. 16, # 36, p. 6647 - 6651
  • 3
  • [ 25235-85-2 ]
  • [ 876-72-2 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 9, p. 3696 - 3708
[2] Patent: US6433175, 2002, B1,
[3] Patent: US2007, 2001, H1,
  • 4
  • [ 25235-85-2 ]
  • [ 41910-64-9 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: With sodium cyanoborohydride; acetic acid In N,N-dimethyl-formamide at 20℃; for 2 h;
Stage #2: With water; sodium hydroxide In N,N-dimethyl-formamide
General procedure: 5.1.24. 7-Fluoro-2,3-dihydro-1H-indole (15f) 7-Fluoro-1H-indole (20.0 g, 148 mmol) was dissolved in acetic acid (60 mL) and sodium cyanoborohydride (18.7 g, 296 mmol) was added in portions. The mixture was stirred for 2 h and then poured into 1500 mL of 2 M aqueous NaOH solution. The mixture was extracted with CH2Cl2. The organic layers were combined, washed with brine, dried over MgSO4, and concentrated under reduced pressure to give the title compound (20.0 g, 98percent). 1H NMR (400 MHz, CDCl3) δ 3.08 (2H, t, J = 8.4 Hz), 3.62 (2H, t, J = 8.4 Hz), 6.62-6.66 (1H, m), 6.78-6.83 (1H, m), 6.90 (1H, dd, J = 7.6, 0.4 Hz).
Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 5, p. 1649 - 1666
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 1, p. 166 - 178
[3] Journal of Medicinal Chemistry, 1998, vol. 41, # 10, p. 1598 - 1612
[4] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 21, p. 3105 - 3109
[5] Patent: US2008/27014, 2008, A1, . Location in patent: Page/Page column 39
[6] Patent: US2008/27122, 2008, A1, . Location in patent: Page/Page column 11
[7] Patent: WO2011/119663, 2011, A1, . Location in patent: Page/Page column 241
[8] Patent: WO2012/163456, 2012, A1, . Location in patent: Page/Page column 27-28; 31-32
[9] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 2425 - 2437
  • 5
  • [ 25235-85-2 ]
  • [ 64-19-7 ]
  • [ 41910-64-9 ]
  • [ 860024-86-8 ]
Reference: [1] Patent: WO2012/163456, 2012, A1, . Location in patent: Page/Page column 27-28; 31-32
[2] Patent: WO2012/163792, 2012, A1, . Location in patent: Page/Page column 26; 29
  • 6
  • [ 25235-85-2 ]
  • [ 73183-34-3 ]
  • [ 388116-27-6 ]
YieldReaction ConditionsOperation in experiment
80% With N-ethyl-N,N-diisopropylamine; triphenylphosphine In methanol at 20 - 50℃; Inert atmosphere Under a nitrogen atmosphere, a reaction vessel of 20 ml in volume was charged with bis(pinacolate)diboron (0.50 g (2.0 mmol)), degassed methanol (7.2 g) and diisopropylethylamine (0.51 g (4.0 mmol)) and stirred at room temperature. The reaction vessel was charged with bis(l,5-cyclooctadiene)nickel (15 mg (0.05 mmol)), triphenylphosphine (28 mg (0.11 mmol)), and 4-chloroindole (0.20 g (1.32 mmol)) and stirred at 300C for 21 hours, and thereafter stirred at 500C for 3 hours. The reaction solution was analyzed by gas chromatography. As a result, 4-(4,4,5,5-tetramethyl- 1,3,2- dioxaborolan-2-yl)indole was contained in an amount of 0.26 g (1.05 mmol, yield:80percent).
80% With N-ethyl-N,N-diisopropylamine; triphenylphosphine In methanol at 20 - 50℃; for 24 h; Inert atmosphere Under a nitrogen atmosphere, a reaction vessel of 20 ml in volume was charged with bis(pinacolate)diboron (0.50 g (2.0 mmol)), degassed methanol (7.2 g) and diisopropylethylamine (0.51 g (4.0 mmol)) and stirred at room temperature. The reaction vessel was charged with bis(1,5-cyclooctadiene)nickel (15 mg (0.05 mmol)), triphenylphosphine (28 mg (0.11 mmol)), and 4-chloroindole (0.20 g (1.32 mmol)) and stirred at 30° C. for 21 hours, and thereafter stirred at 50° C. for 3 hours. The reaction solution was analyzed by gas chromatography. As a result, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole was contained in an amount of 0.26 g (1.05 mmol, yield: 80percent).
Reference: [1] Patent: WO2010/110782, 2010, A1, . Location in patent: Page/Page column 47
[2] Patent: US2012/123122, 2012, A1, . Location in patent: Page/Page column 13-14
[3] Tetrahedron, 2001, vol. 57, # 49, p. 9813 - 9816
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