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[ CAS No. 75400-67-8 ] {[proInfo.proName]}

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Chemical Structure| 75400-67-8
Chemical Structure| 75400-67-8
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Product Details of [ 75400-67-8 ]

CAS No. :75400-67-8 MDL No. :MFCD02093939
Formula : C13H15NO2 Boiling Point : -
Linear Structure Formula :C8H6NCOOC(CH3)3 InChI Key :OWPIFQXNMLDXKW-UHFFFAOYSA-N
M.W : 217.26 Pubchem ID :3532980
Synonyms :

Calculated chemistry of [ 75400-67-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.31
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 64.14
TPSA : 31.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.87
Log Po/w (XLOGP3) : 3.27
Log Po/w (WLOGP) : 3.42
Log Po/w (MLOGP) : 2.63
Log Po/w (SILICOS-IT) : 2.06
Consensus Log Po/w : 2.85

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.47
Solubility : 0.0744 mg/ml ; 0.000342 mol/l
Class : Soluble
Log S (Ali) : -3.6
Solubility : 0.0545 mg/ml ; 0.000251 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.37
Solubility : 0.0938 mg/ml ; 0.000432 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.89

Safety of [ 75400-67-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 75400-67-8 ]

* 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 [ 75400-67-8 ]
  • Downstream synthetic route of [ 75400-67-8 ]

[ 75400-67-8 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 75400-67-8 ]
  • [ 26340-49-8 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1985, vol. 22, # 2, p. 505 - 509
  • 2
  • [ 110-18-9 ]
  • [ 75400-67-8 ]
  • [ 57476-50-3 ]
Reference: [1] ACS Catalysis, 2014, vol. 4, # 6, p. 1897 - 1900
  • 3
  • [ 75400-67-8 ]
  • [ 192189-07-4 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 38, p. 6849 - 6852
  • 4
  • [ 5419-55-6 ]
  • [ 75400-67-8 ]
  • [ 213318-44-6 ]
YieldReaction ConditionsOperation in experiment
67% With lithium diisopropyl amide In diethyl ether at -70℃; Step 2:
1-(tert-Butoxycarbonyl)-1H-indol-2-ylboronic acid
Lithium diisopropylamide (140 mL) was added dropwise to a mixture of tert-butyl 1H-indole-1-carboxylate (26 g, 119.67 mmol) and triisopropyl borate (30 g, 159.57 mmol) in ethoxyethane (500 mL) at -70° C.
The resulting solution was stirred at -70° C. (reaction progress monitored by TLC (EtOAc/PE=1:5)).
The reaction mixture was then quenched by the adding 200 g of water/ice.
Adjustment of the pH to 7 was accomplished by the addition of HCl (10percent).
The resulting solution was extracted with Ether (1*100 mL) and the organic layers were combined and dried over Na2SO4 to afford 13 g (67percent) of 1-(tert-butoxycarbonyl)-1H-indol-2-ylboronic acid as a white solid.
74 g
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at 0 - 20℃; Inert atmosphere
Stage #2: With hydrogenchloride In tetrahydrofuran
Under a nitrogen atmosphere, 63.3 g (290 mmol) of the intermediate (A-2), 99.6 g (530 mmol) of triisopropyl borate (B(OiPr)3), and 370 ml of THF were loaded and the mixture was cooled to 0°C. To the resultant solution were added dropwise 185 ml (2.0 mol/l) of a solution of lithium diisopropyl amide (LDA) in THF. The reaction solution was returned to room temperature and stirred for 2 hr. After that, to the resultant solution were added 370 ml of 2 N hydrochloric acid and the aqueous layer was separated from the organic layer. The aqueous layer was extracted with THF (300 ml) and the combined organic layer was dried over anhydrous magnesium sulfate. The magnesium sulfate was separated by filtration and the solvent was removed by evaporation under reduced pressure to give 74.0 g (283 mmol, yield: 98 molpercent) of an intermediate (A-3).
Reference: [1] Organic and Biomolecular Chemistry, 2007, vol. 5, # 8, p. 1218 - 1227
[2] Patent: US2008/139558, 2008, A1, . Location in patent: Page/Page column 67
[3] Patent: EP2687530, 2014, A1, . Location in patent: Paragraph 0096
  • 5
  • [ 75400-67-8 ]
  • [ 213318-44-6 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 14, p. 5046 - 5055
[2] Organic and Biomolecular Chemistry, 2007, vol. 5, # 8, p. 1218 - 1227
[3] Chemical Communications, 2008, # 16, p. 1865 - 1867
[4] Tetrahedron, 1998, vol. 54, # 46, p. 14081 - 14088
[5] Tetrahedron, 2007, vol. 63, # 10, p. 2263 - 2274
[6] Journal of Organic Chemistry, 2002, vol. 67, # 21, p. 7551 - 7552
[7] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 11, p. 1705 - 1713
[8] Tetrahedron, 2009, vol. 65, # 34, p. 6877 - 6881
[9] Patent: WO2005/40133, 2005, A1, . Location in patent: Page/Page column 155-156
  • 6
  • [ 768-66-1 ]
  • [ 75400-67-8 ]
  • [ 213318-44-6 ]
YieldReaction ConditionsOperation in experiment
37% With n-butyllithium In tetrahydrofuran; hexane EXAMPLE 5
Compound (III)
To a solution of 2,2,6,6-tetramethylpiperidine (11.0 g; 78 mmols) in THF (170 ml), at -78° C. and under nitrogen, a 1.6M solution of BuLi (56.1 ml; 89.7 mmols) in hexane is added slowly in order to maintain the temperature below -65° C.
The mixture is stirred at -75° C. for 10 min and is then warmed to 0° C. within 30 min.
After cooling again to -78° C., a solution of 1-tert-butoxycarbonylindole (15.6 g; 72 mmols) in THF (300 ml) is added, keeping the temperature below -65° C.
The mixture is stirred 1 hour at -75° C. and a solution of trimrthyl borate (7.5 g; 72 mmols) in THF (200 ml) is added dropwise.
The reaction is allowed to warm up to room temperature overnight.
A 0.25N solution of Hcl (200 ml) is added and the THF is removed under vacuum.
The residue is extracted with ethyl ether (3*150 ml) and the combined organic phases are washed with water (2*100 ml) and dried over sodium sulphate.
The solution is then concentrated, cooled to 0° C. and filtered to obtain crystalline (1-tert-butoxycarbonylindol-2-yl)boronic acid (6.95 g; 26.6 mmols). Yield: 37percent.
1 NMR (400 mhz, CDCl3), ppm:
1.73 (9H, s), 7.31 (2H, m), 7.56 (2H, m), 7.57 (2H, bs) 8.01 (1H, bd, J=8.2 Hz).
Reference: [1] Patent: US6071947, 2000, A,
  • 7
  • [ 75400-67-8 ]
  • [ 198135-71-6 ]
  • [ 219552-64-4 ]
Reference: [1] Synthesis, 1999, # 7, p. 1117 - 1122
[2] Synthesis, 1999, # 7, p. 1117 - 1122
  • 8
  • [ 75400-67-8 ]
  • [ 25015-63-8 ]
  • [ 942070-45-3 ]
Reference: [1] Organometallics, 2014, vol. 33, # 13, p. 3514 - 3522
[2] Journal of Organic Chemistry, 2009, vol. 74, # 23, p. 9199 - 9201
  • 9
  • [ 75400-67-8 ]
  • [ 73183-34-3 ]
  • [ 942070-45-3 ]
Reference: [1] Organometallics, 2014, vol. 33, # 13, p. 3514 - 3522
[2] Journal of the American Chemical Society, 2015, vol. 137, # 25, p. 8058 - 8061
[3] Angewandte Chemie - International Edition, 2012, vol. 51, # 2, p. 540 - 543
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