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[ CAS No. 10075-48-6 ] {[proInfo.proName]}

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Chemical Structure| 10075-48-6
Chemical Structure| 10075-48-6
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Product Details of [ 10075-48-6 ]

CAS No. :10075-48-6 MDL No. :MFCD04038746
Formula : C9H8BrN Boiling Point : -
Linear Structure Formula :- InChI Key :GDQXDVJFMLNXHX-UHFFFAOYSA-N
M.W : 210.07 Pubchem ID :254707
Synonyms :

Calculated chemistry of [ 10075-48-6 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.11
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.96
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) : -5.38 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.03
Log Po/w (XLOGP3) : 3.1
Log Po/w (WLOGP) : 3.24
Log Po/w (MLOGP) : 2.61
Log Po/w (SILICOS-IT) : 3.67
Consensus Log Po/w : 2.93

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.7
Solubility : 0.0418 mg/ml ; 0.000199 mol/l
Class : Soluble
Log S (Ali) : -3.1
Solubility : 0.167 mg/ml ; 0.000795 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.53
Solubility : 0.00621 mg/ml ; 0.0000296 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.23

Safety of [ 10075-48-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 10075-48-6 ]

* 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 [ 10075-48-6 ]
  • Downstream synthetic route of [ 10075-48-6 ]

[ 10075-48-6 ] Synthesis Path-Upstream   1~12

  • 1
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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
  • 2
  • [ 87-48-9 ]
  • [ 10075-48-6 ]
Reference: [1] Patent: US5252732, 1993, A,
[2] Patent: US5349061, 1994, A,
  • 3
  • [ 67-56-1 ]
  • [ 10075-50-0 ]
  • [ 10075-48-6 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 19, p. 5228 - 5231
[2] RSC Advances, 2015, vol. 5, # 86, p. 70329 - 70332
  • 4
  • [ 10075-50-0 ]
  • [ 10075-48-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 3, p. 333 - 336
[2] Patent: WO2012/119046, 2012, A2,
[3] ChemMedChem, 2012, vol. 7, # 12, p. 2179 - 2193
[4] Angewandte Chemie - International Edition, 2013, vol. 52, # 11, p. 3250 - 3254[5] Angew. Chem., 2013, vol. 125, # 11, p. 3332 - 3336,5
[6] Chemistry - A European Journal, 2015, vol. 21, # 43, p. 15104 - 15107
  • 5
  • [ 589-21-9 ]
  • [ 10075-48-6 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 11, p. 2958 - 2961
  • 6
  • [ 125914-22-9 ]
  • [ 10075-48-6 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 21, p. 5508 - 5511
  • 7
  • [ 586-78-7 ]
  • [ 10075-48-6 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 21, p. 5508 - 5511
  • 8
  • [ 92557-51-2 ]
  • [ 10075-48-6 ]
Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 24, p. 7492 - 7500
  • 9
  • [ 622-88-8 ]
  • [ 10075-48-6 ]
Reference: [1] Synthetic Communications, 1993, vol. 23, # 14, p. 2011 - 2017
  • 10
  • [ 70070-22-3 ]
  • [ 10075-48-6 ]
Reference: [1] Synthetic Communications, 1993, vol. 23, # 14, p. 2011 - 2017
  • 11
  • [ 10075-48-6 ]
  • [ 75-03-6 ]
  • [ 10075-49-7 ]
YieldReaction ConditionsOperation in experiment
93.2%
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 0 - 5℃; for 1.1 h;
Stage #2: at 0 - 20℃; for 18 h;
Product is prepared according to procedure described in literature (Fraile, J. M.; Le Jeune, K.; Mayoral, J. A.; Ravasio, N.; Zaccheria, F.; Org. Biomol. Chem. 2013, v:11 , pp: 4327-4332). A solution of 5-bromo-3-methyl-1 H-indole (0.30 g; 1.437 mmol; 1.00 eqf.) in dry THF (5.0 ml), is cooled to 0-5°C then NaH (60percent immersion in mineral oil) (0.14 g; 2.86 mmol; 2.00 eqf.) is added in small portions over 10 min. RM is stirred for 1 h then lodoethane (0.21 ml; 2.86 mmol; 2.0 eqf.) is added dropwise. Reaction mixture is stirred for next 30 min at 0°C and 18 h at rt. After mentioned time RM is poured onto ice and extracted with diethyl ether. Organic layers is washed with brine and dried over Na2S04. Solvent is evaporated in vacuo to provide desired product 5- bromo-1 ,3-dimethyl-1 H-indole (0.355 g; 1.33 mmol; yield 93.2percent; 84percent by UPLC) is obtained as light yellow oil.
Reference: [1] Patent: WO2016/180536, 2016, A1, . Location in patent: Page/Page column 292
  • 12
  • [ 10075-48-6 ]
  • [ 74-88-4 ]
  • [ 10075-49-7 ]
Reference: [1] Journal of the American Chemical Society, 2010, vol. 132, # 41, p. 14418 - 14420
[2] Organic Letters, 2014, vol. 16, # 11, p. 2958 - 2961
[3] Journal of the American Chemical Society, 2015, vol. 137, # 47, p. 14861 - 14864
[4] Patent: US5252732, 1993, A,
[5] Chemistry - A European Journal, 2015, vol. 21, # 43, p. 15104 - 15107
[6] Patent: US5349061, 1994, A,
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