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[ CAS No. 877-03-2 ] {[proInfo.proName]}

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Chemical Structure| 877-03-2
Chemical Structure| 877-03-2
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Product Details of [ 877-03-2 ]

CAS No. :877-03-2 MDL No. :MFCD00152016
Formula : C9H6BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :PEENKJZANBYXNB-UHFFFAOYSA-N
M.W : 224.05 Pubchem ID :70137
Synonyms :

Calculated chemistry of [ 877-03-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.39
TPSA : 32.86 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) : -6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.59
Log Po/w (XLOGP3) : 2.2
Log Po/w (WLOGP) : 2.74
Log Po/w (MLOGP) : 1.6
Log Po/w (SILICOS-IT) : 3.33
Consensus Log Po/w : 2.29

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.1
Solubility : 0.176 mg/ml ; 0.000787 mol/l
Class : Soluble
Log S (Ali) : -2.52
Solubility : 0.67 mg/ml ; 0.00299 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.09
Solubility : 0.0182 mg/ml ; 0.0000811 mol/l
Class : Moderately soluble

Medicinal Chemistry

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

Safety of [ 877-03-2 ]

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 [ 877-03-2 ]

* 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 [ 877-03-2 ]
  • Downstream synthetic route of [ 877-03-2 ]

[ 877-03-2 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 877-03-2 ]
  • [ 827-01-0 ]
Reference: [1] Journal of the Korean Chemical Society, 2011, vol. 55, # 2, p. 240 - 242
[2] Journal of the Korean Chemical Society, 2011, vol. 55, # 2, p. 317 - 322
  • 2
  • [ 877-03-2 ]
  • [ 90271-86-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 2, p. 363 - 371
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 10, p. 2948 - 2950
[3] Patent: US6541505, 2003, B1,
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 19, p. 5897 - 5900
[5] Green Chemistry, 2018, vol. 20, # 1, p. 266 - 273
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  • [ 877-03-2 ]
  • [ 108-03-2 ]
  • [ 468717-36-4 ]
  • [ 90271-86-6 ]
YieldReaction ConditionsOperation in experiment
65% With sodium hydroxide In acetic acid EXAMPLE 153
5-(2-Dimethylaminomethyl-cyclopropylmethyl)-1H-indole-3-carbonitrile
Commercially available 5-bromoindole-3-carboxaldehyde (11.3 g, 50.4 mmol), ammonium hydrogen phosphate (47.0 g, 353 mmol), 1-nitropropane (4.49 g, 50.4 mmol), and glacial acetic acid (100 ml) were heated at a gentle reflux for 18 h.
The resulting mixture was concentrated in vacuo and the residue mixed with 5 N sodium hydroxide (500 ml) and ice chips.
The precipitate was collected by filtration and rinsed several times with water.
The filtrate was concentrated in vacuo to afford 5-bromo-3-cyanoindole (7.23 g, 65percent) as a dark solid. 1H-NMR (400 MHz, CDCl3) δ10.0 (1 H, s), 8.68 (1 H, br s), 8.51 (1 H, s), 7.85 (1 H, s), 7.43 (1 H, dd, J=8.6, 1.9 Hz), 7.32 (1 H, d, J=8.6 Hz).
Reference: [1] Patent: US2003/73849, 2003, A1,
  • 4
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  • [ 90271-86-6 ]
Reference: [1] Patent: US2004/204397, 2004, A1,
  • 5
  • [ 877-03-2 ]
  • [ 773887-02-8 ]
  • [ 90271-86-6 ]
YieldReaction ConditionsOperation in experiment
87% With acetic acid In water; 1-Nitropropane 5-Bromo-7-methyl-1H-indole-3-carbonitrile
A mixture of 5-bromo-indole-3-carboxaldehyde (0.7 g, 2.94 mmol), diammonium hydrogen phosphate (2.05 g, 15.5 mmol) in 1-nitropropane (9 mL) and acetic acid (3 mL) were heated at reflux for 16 h.
After cooling to room temperature, the solvents were removed under reduced pressure and water added to the dark residue.
After a short while, 5-bromo-1H-indole-3-carbonitrile precipitated rapidly, was filtered, washed severally with water and dried for several hours to afford 0.6 g (87percent) of the desired nitrile. LC/MS: tR=1.71 min, 235.01 (MH)+.
Reference: [1] Patent: US2004/204397, 2004, A1,
  • 6
  • [ 877-03-2 ]
  • [ 10406-06-1 ]
YieldReaction ConditionsOperation in experiment
65% With potassium permanganate; water In acetone at 20℃; for 6.5 h; General procedure: 6 g of substituted indole-3-aldehydes (10a–b) was dissolved in 600 mL of acetone.To this KMnO4 (9 g, 56 mmol) soluble in 180 mL water was added slowly for 30 min and the reaction mixture was allowed for stirring for 6 h at room temperature. After it was quenched by 6 mL of 30percent H2O2, filtered and concentrated on rotavapor. Now it was solidified by conc.HCl, filtered, dried and recrystallized from methanol solvent which then afforded 5-substituted indole-3-carboxylic acids 11a–b. 5-Bromo-1H-indole-3-carboxylic acid (11b) (Yoo et al.2012) yellow color solid. yield: 65percent. m.p: 230–232 °C; IR (KBr): 3349, 2914, 2574, 1643 cm−1; 1H NMR (400 MHz, DMSO-d6): δ 7.30 (1H, m, Ar–H), 7.435 (1H, d, J = 8.8 Hz, Ar–H), 8.05 (1H, d, J = 2.8 Hz, Ar–H), 8.12 (1H, d, J = 2 Hz, Ar–H), 12.01 (1H, bs, -NH), 12.13 (1H, s, -OH) ppm; 13C NMR (400 MHz, DMSO-d6): δ 107.06, 113.79, 114.28, 122.68, 124.70, 127.79, 133.45, 135.16, 165.45 ppm; HRMS calculated for C9H6NO2BrNa: 261.94741; found: 261.94711.
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 7, p. 2745 - 2763
[2] Chemical Papers, 2018, vol. 72, # 6, p. 1369 - 1378
  • 7
  • [ 877-03-2 ]
  • [ 10075-48-6 ]
YieldReaction ConditionsOperation in experiment
82% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 70℃; for 2 h; (d) 5,5'-Dibromo-3,3'-dimethyl-2,2'-diindolylmethane (42). To a solution of aldehyde 40 (1.51 g, 6.74 mmol) in THF (35 mL) was added LiAlH4 (0.51 g, 13.48 mmol) at 0° C. and then heated to 65-70° C. for 2 h under argon. The suspension was cooled to 0° C. and quenched with water, and white precipitate was removed by filtration. The filtrate was dried (MgSO4) and concentrated to afford 5-bromo-3-methylindole (41) as a solid (1.16 g, 82percent). To a mixture of 39 (1.2 g, 5.0 mmol) and 41 (1.0 g, 4.76 mmol) in CH2Cl2 (25 mL) was added (CF3SO3)3Sc (0.23 g, 0.47 mmol) and stirred overnight under argon. The solvent was evaporated to give a crude product. Flash chromatography (10percent EtOAc/hexane) yielded 42 as a white solid (1.91 g, 93percent): 1H NMR (300 MHz, CDCl3) δ 2.29 (s, 6, CH3), 4.21 (s, 2, CH2), 7.08 (d, J=8.5 Hz, 2, ArH), 7.22 (dd, J=1.8, 8.5 Hz, 2, ArH), 7.66 (d, J=1.8 Hz, 2, ArH), 7.67 (br.s, 2, NH).
73% With lithium aluminium tetrahydride In tetrahydrofuran for 2 h; Reflux Ste 2. 5-Bromo-3-methyl-7H-indoleTo a solution of 5-bromo-7H-indole-3-carbaldehyde (5.0 g, 22.3 mmol) in THF (80 mL) was added L1AIH4 (1.70 g, 44.6 mmol). The resulting solution was stirred for 2h under reflux, then poured into IN NaOH solution (150 mL), extracted with ethyl acetate (3 x 100 mL), dried over anhydrous sodium sulfate, and then concentrated under vacuum to give a residue, which was purified via silica gel chromatography (3percent ethyl acetate in petroleum ether) to afford 5-bromo-3-methyl-7H-indole as a white solid (3.4 g, 73percent).'H-NMR (300 MHz, CDCI3): 5:7.91 (s, 1H), 7.72 - 7.73 (t, /= 0.9 Hz, 1H), 7.21 - 7.30 (m, 2H), 6.99 (d, /= 0.9 Hz, 1H), 2.31 (s, 3H)
44.7% With lithium aluminium tetrahydride In tetrahydrofuran for 8.5 h; Reflux A solution of 5-bromo-1H-indole-3-carbaldehyde (13.12 g, 58.6 mmol) in THF (100 mL) was added to a refluxing mixture of LiA1H4 (4.89 g, 129 mmol) in THF (100 mL) (reflux condenser fitted to a two neck flask) over 30 mm. The reaction mixture was refluxed for 8 hours, cooled to room temperature and treated with diethyl ether (50 mL). The reaction mixture was acidified to pH 3 with iN HC1, while cooling in an ice bath. The reaction mixture was diluted with ethyl acetate (125 mL), poured into a separatory funnel and washed with water (2X 50 mL) and saturated aqueous sodium chloridesolution (50 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give crude product. The crude product was dissolved in a small amount of DCM and charged to an ISCO silica gel (80 g) column, which was eluted over 15 minutes using a gradient of 0-50percent ethyl acetate/heptane. The combined fractions were concentrated to give 5-bromo-3-methyl-1H-indole (5.5 g, 44.7percent yield). LCretention time 1.0 mm [Method Al]. MS (E) m/z: 210/212 (M-H).
Reference: [1] Patent: US2004/43965, 2004, A1, . Location in patent: Page/Page column 21-22
[2] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 3, p. 333 - 336
[3] Patent: WO2012/119046, 2012, A2, . Location in patent: Page/Page column 184
[4] ChemMedChem, 2012, vol. 7, # 12, p. 2179 - 2193
[5] Patent: WO2018/26620, 2018, A1, . Location in patent: Page/Page column 77; 78
[6] Angewandte Chemie - International Edition, 2013, vol. 52, # 11, p. 3250 - 3254[7] Angew. Chem., 2013, vol. 125, # 11, p. 3332 - 3336,5
[8] Chemistry - A European Journal, 2014, vol. 20, # 24, p. 7492 - 7500
[9] Angewandte Chemie - International Edition, 2014, vol. 53, # 44, p. 11881 - 11885[10] Angew. Chem., 2014, vol. 126, # 44, p. 12075 - 12079,5
[11] Organic Letters, 2015, vol. 17, # 11, p. 2652 - 2655
[12] Chemistry - A European Journal, 2015, vol. 21, # 43, p. 15104 - 15107
[13] Organic Letters, 2017, vol. 19, # 1, p. 222 - 225
  • 8
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  • [ 10075-49-7 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 43, p. 15104 - 15107
  • 9
  • [ 487-89-8 ]
  • [ 877-03-2 ]
  • [ 17826-04-9 ]
  • [ 17900-95-7 ]
Reference: [1] Environmental Toxicology and Chemistry, 2001, vol. 20, # 3, p. 589 - 596
  • 10
  • [ 487-89-8 ]
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  • [ 17826-04-9 ]
Reference: [1] Journal of Chemical Ecology, 1997, vol. 23, # 11, p. 2507 - 2521
  • 11
  • [ 877-03-2 ]
  • [ 400071-95-6 ]
Reference: [1] European Journal of Medicinal Chemistry, 2001, vol. 36, # 6, p. 545 - 553
  • 12
  • [ 877-03-2 ]
  • [ 24424-99-5 ]
  • [ 325800-39-3 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 44, p. 7717 - 7719
[2] Tetrahedron, 2002, vol. 58, # 15, p. 3101 - 3110
[3] Journal of Organic Chemistry, 2014, vol. 79, # 15, p. 7122 - 7131
[4] Chemical Papers, 2016, vol. 70, # 5, p. 635 - 648
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  • [ 773873-77-1 ]
Reference: [1] Chemical Papers, 2018, vol. 72, # 6, p. 1369 - 1378
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