610794-15-5|4-Bromo-5-methyl-1H-indole| Ambeed

Structure of 610794-15-5

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Quality Control of [ 610794-15-5 ] Purity: 98% SDS Specification

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Product Details of [ 610794-15-5 ]

CAS No. :	610794-15-5
Formula :	C₉H₈BrN
M.W :	210.07
SMILES Code :	CC1=C(Br)C2=C(NC=C2)C=C1
MDL No. :	MFCD11878622
InChI Key :	DVCLJDAZHYRZHZ-UHFFFAOYSA-N
Pubchem ID :	10488635

Safety of [ 610794-15-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H317
Precautionary Statements:	P280

Computational Chemistry of [ 610794-15-5 ] Show Less

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 ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	15.79 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.0
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.1
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.24
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.61
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.67
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.92

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.7
Solubility	0.0418 mg/ml ; 0.000199 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.1
Solubility	0.167 mg/ml ; 0.000795 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-4.53
Solubility	0.00621 mg/ml ; 0.0000296 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.38 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.44

Application In Synthesis of [ 610794-15-5 ]

* 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 [ 610794-15-5 ]
Downstream synthetic route of [ 610794-15-5 ]

[ 610794-15-5 ] Synthesis Path-Upstream 1~10

1
[ 1063613-39-7 ]
[ 610794-15-5 ]

Yield	Reaction Conditions	Operation in experiment
20%	With acetic acid; zinc In water at 0 - 110℃;	[2-(2-Bromo-3-methyl-6-nitro-phenyl)-vinyl]-dimethyl-amine (10 g) was dissolved in AcOH /H₂O(100mL:25mL), cooled to 0°C and treated with Zn (30 g) added slowly in portions. After complete addition, the reaction mixture was heated at 110°C overnight. The mixture was diluted with water and extracted with EtOAc. The organic layer was dried over Na₂S0 and concentrated to give the crude product. The crude product was purified by silica gel column chromatography to afford the title compound (1.4 g, 20 percent) ¹H NMR CDCI₃400 MHz δ 2.47 (m, 3H), 6.50-6.51 (m, 1H), 6.97-6.99 (m, 1 H), 7.12- 7.18(m, 2H), 8.12 (s, 1 H)
1.4 g	With acetic acid; zinc In water at 0 - 110℃;	2-(2-Bromo-3-methyl-6-nitro-phenyl)vinyl]-dimethyl-amine (10 g) was dissolved in AcOH/H₂O (100 mL:25 mL), cooled to 0° C. and treated with Zn (30 g) added slowly in portions. After complete addition, the reaction mixture was heated at 110° C. overnight. The mixture was diluted with water and extracted with EtOAc. The organic layer was dried over Na₂SO₄ and concentrated to give the crude product. The crude product was purified by silica gel column chromatography to afford the title compound (1.4 g, 20percent) ¹H NMR CDCl₃ 400 MHz δ 2.47 (m, 3H), 6.50-6.51 (m, 1H), 6.97-6.99 (m, 1H), 7.12-7.18 (m, 2H), 8.12 (s, 1H)

References: [1] Patent: WO2013/117522, 2013, A1, . Location in patent: Page/Page column 38.
[2] Patent: US2015/18367, 2015, A1, . Location in patent: Paragraph 0169; 0170.
[3] Patent: WO2005/110416, 2005, A2, . Location in patent: Page/Page column 57.

2
[ 5815-08-7 ]
[ 60956-25-4 ]
[ 610794-15-5 ]

References: [1] Patent: WO2008/79918, 2008, A1, . Location in patent: Page/Page column 61-62.
[2] Patent: WO2003/82826, 2003, A1, . Location in patent: Page/Page column 54.
[3] Patent: WO2005/110991, 2005, A1, . Location in patent: Page/Page column 50-51.

3
[ 60956-25-4 ]
[ 4637-24-5 ]
[ 610794-15-5 ]

Yield	Reaction Conditions	Operation in experiment
5.5%	Stage #1: With pyrrolidine In 1,4-dioxane at 100℃; for 18 h; Inert atmosphere Stage #2: at 110℃; for 4 h;	ep 2: A mixture of 298 (3.0 g, 13.04 mmol), pyrrolidine (926 mg, 13.04 mmol), and DMF-DMA (7.76 g, 65.22 mmol) in 1,4-dioxane (20 mL) under nitrogen atmosphere was heated at 100 °C for 18 h. The reaction was concentrated under to dryness in vacuo and to the residue was added iron (3.65 g, 65.22 mmol) and HO Ac (40 mL). The resulting mixture was heated at 110 °C for 4 h, cooled to RT and filtered. The filtrate was concentrated in vacuo. The crude was purified by S1O₂ chromatography eluting with petroleum ether/EtOAc (10:1) to afford 150 mg (5.5percent) of 4-bromo-5-methyl-lH-indole (300) as a yellow solid: MS (ESI) m/z = 210.1 (M+l).

References: [1] Patent: WO2013/26914, 2013, A1, . Location in patent: Page/Page column 170.

4
[ 926922-44-3 ]
[ 610794-15-5 ]

References: [1] Patent: WO2007/21937, 2007, A2, . Location in patent: Page/Page column 43-44.

5
[ 60956-25-4 ]
[ 717111-91-6 ]
[ 610794-15-5 ]

References: [1] Patent: WO2004/43925, 2004, A2, . Location in patent: Page 68.

6
[ 576-22-7 ]
[ 610794-15-5 ]

References: [1] Patent: WO2013/26914, 2013, A1, .
[2] Patent: WO2013/117522, 2013, A1, .
[3] Patent: US2015/18367, 2015, A1, .
[4] Patent: WO2005/110416, 2005, A2, .
[5] Patent: WO2005/110991, 2005, A1, .

7
[ 7745-91-7 ]
[ 610794-15-5 ]

References: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 10, p. 1598 - 1612.

8
[ 116598-91-5 ]
[ 610794-15-5 ]

References: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 10, p. 1598 - 1612.

9
[ 60956-25-4 ]
[ 610794-15-5 ]

References: [1] Patent: WO2013/117522, 2013, A1, .
[2] Patent: US2015/18367, 2015, A1, .
[3] Patent: WO2005/110416, 2005, A2, .

10
[ 109179-31-9 ]
[ 610794-15-5 ]

References: [1] Patent: US2016/9706, 2016, A1, .