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[ CAS No. 773873-77-1 ] {[proInfo.proName]}

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Chemical Structure| 773873-77-1
Chemical Structure| 773873-77-1
Structure of 773873-77-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 773873-77-1 ]

CAS No. :773873-77-1 MDL No. :MFCD06203728
Formula : C10H8BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :MFOKOKHNSVUKON-UHFFFAOYSA-N
M.W : 254.08 Pubchem ID :285091
Synonyms :

Calculated chemistry of [ 773873-77-1 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.1
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 57.28
TPSA : 42.09 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) : -6.01 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.21
Log Po/w (XLOGP3) : 2.59
Log Po/w (WLOGP) : 2.72
Log Po/w (MLOGP) : 2.08
Log Po/w (SILICOS-IT) : 3.02
Consensus Log Po/w : 2.52

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.39
Solubility : 0.103 mg/ml ; 0.000407 mol/l
Class : Soluble
Log S (Ali) : -3.12
Solubility : 0.192 mg/ml ; 0.000754 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.22
Solubility : 0.0155 mg/ml ; 0.0000608 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.6

Safety of [ 773873-77-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 773873-77-1 ]

* 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.

  • Upstream synthesis route of [ 773873-77-1 ]
  • Downstream synthetic route of [ 773873-77-1 ]

[ 773873-77-1 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 773873-77-1 ]
  • [ 400071-95-6 ]
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 51, p. 7114 - 7117
  • 2
  • [ 67-56-1 ]
  • [ 773873-77-1 ]
YieldReaction ConditionsOperation in experiment
86% With potassium hydroxide In water at 85℃; for 3 h; General procedure: To a solution of compounds 21(b-c) (1 equiv) in MeOH, a solution of KOH in water was added. The reaction mixture was refluxed for 3 h. The solvents were removed under reduced pressure, the residue was partitioned between EtOAc and 1 N aq. HCl and the layers were separated. The aqueous layer was washed with EtOAc (3×) and the combined organic phases were washed with brine (1×), dried over anhydrous Na2SO4, filtered and concentrated to near dryness. The crude residue was purified by silica gel flash column chromatography eluted with mixtures of MeOH in dichloromethane to afford the corresponding methyl esters 22(b-c).
Reference: [1] Tetrahedron, 2016, vol. 72, # 19, p. 2376 - 2385
[2] Organic Letters, 2016, vol. 18, # 24, p. 6504 - 6507
  • 3
  • [ 67-56-1 ]
  • [ 10075-50-0 ]
  • [ 76-02-8 ]
  • [ 773873-77-1 ]
Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 48, p. 16162 - 16163
[2] European Journal of Medicinal Chemistry, 2013, vol. 64, p. 498 - 511
[3] Medicinal Chemistry Research, 2013, vol. 22, # 9, p. 4492 - 4504
  • 4
  • [ 67-56-1 ]
  • [ 10406-06-1 ]
  • [ 773873-77-1 ]
YieldReaction ConditionsOperation in experiment
62% for 5 h; Reflux General procedure: 4 g of 5-substituted indole- 3- carboxylic acids was dissolved in 10 volumes(400 mL) of methanol and catalytic amount of conc.H2SO4 was added slowly. The total reaction mixture was refluxed over 5 h time period and the reaction mixture was cooled to room temperature slowly. Now ice cold water was added and the yellow color solid was filtered. This solid was recrystallized from ethanol yielded 5 -substituted -3- carbomethoxyindoles 12a–b. Methyl-5-bromo-1H-indole-3-carboxylate (12b) yellow color solid. yield 62percent. m.p: 210–212 °C; IR (KBr): 3213, 3114, 2929, 1745 cm−1; 1H NMR (400 MHz, CDCl3): δ 3.93 (3H, s, -OCH3), 7.28 (1H, d, J = 8.8 Hz, Ar–H),7.35 (1H, m, Ar–H), 7.91 (1H, d, J = 2.8 Hz, Ar–H), 8.32 (1H, s, Ar–H), 8.67 (1H, s, -NH) ppm; 13C NMR (400 MHz, CDCl3+ DMSO-d6): δ 49.93, 105.91, 112.88, 113.75, 122.40, 124.26, 126.65, 131.89, 134.33, 164.13 ppm; HRMS calculated for C10H9NO2Br: 253.98112; found: 253.98102.
Reference: [1] Chemical Papers, 2018, vol. 72, # 6, p. 1369 - 1378
  • 5
  • [ 1262150-42-4 ]
  • [ 773873-77-1 ]
Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 22, p. 11155 - 11162
  • 6
  • [ 10075-50-0 ]
  • [ 773873-77-1 ]
Reference: [1] Tetrahedron, 2016, vol. 72, # 19, p. 2376 - 2385
[2] Organic Letters, 2016, vol. 18, # 24, p. 6504 - 6507
[3] Chemical Papers, 2018, vol. 72, # 6, p. 1369 - 1378
  • 7
  • [ 106-40-1 ]
  • [ 773873-77-1 ]
Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 22, p. 11155 - 11162
  • 8
  • [ 877-03-2 ]
  • [ 773873-77-1 ]
Reference: [1] Chemical Papers, 2018, vol. 72, # 6, p. 1369 - 1378
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