1075-34-9|5-Bromo-2-methylindole| Ambeed

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Quality Control of [ 1075-34-9 ] Purity: 98% SDS Specification

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Product Details of [ 1075-34-9 ]

CAS No. :	1075-34-9
Formula :	C₉H₈BrN
M.W :	210.07
SMILES Code :	CC(N1)=CC2=C1C=CC(Br)=C2
MDL No. :	MFCD01863677
InChI Key :	BJUZAZKEDCDGRW-UHFFFAOYSA-N
Pubchem ID :	5003968

Safety of [ 1075-34-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 1075-34-9 ] 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.	2.14
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	3.14
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	2.96

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.73
Solubility	0.0395 mg/ml ; 0.000188 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.	-3.14
Solubility	0.152 mg/ml ; 0.000722 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	Yes
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.	-5.35 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)	1.28

Application In Synthesis of [ 1075-34-9 ]

* 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.

Downstream synthetic route of [ 1075-34-9 ]

[ 1075-34-9 ] Synthesis Path-Downstream 1~35

1
[ 1075-34-9 ]
[ 50-00-0 ]
[ 124-40-3 ]
[ 100387-87-9 ]

References: [1]Zhurnal Obshchei Khimii,1959,vol. 29,p. 2541,2550; engl. Ausg. S. 2504, 2511.

2
[ 99847-70-8 ]
[ 1075-34-9 ]

References: [1]Zhurnal Obshchei Khimii,1959,vol. 29,p. 2541,2550; engl. Ausg. S. 2504, 2511.

3
[ 67-64-1 ]
[ 589-21-9 ]
[ 1075-34-9 ]

References: [1]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1954,vol. 297,p. 229,233.

4
[ 500-22-1 ]
[ 1075-34-9 ]
5-Bromo-2-methyl-3-(pyridin-3-ylmethyl)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylsilane; In methanol; dichloromethane; trifluoroacetic acid;	PREPARATION 8 5-Bromo-2-methyl-3-(3-pyridylmethyl)-1H-indole A solution of <strong>[1075-34-9]5-bromo-2-methyl-1H-indole</strong> (J. Chem. Soc., 1428 (1965)) (2.0 g) and 3-pyridinecarboxaldehyde (1.02 g) in dry dichloromethane (20 ml) was added dropwise over 10 minutes to a stirred solution of triethylsilane(3.30 g) in trifluoroacetic acid (20 ml) at 0° C. The solution was stirred at 0° C. for 30 minutes and then evaporated under vacuum, keeping the temperature below 35° C. The residue was dissolved in dichloromethane, and the solution was washed with 2N sodium hydroxide, water and dried (MgSO4). The solution was evaporated and the residue was chromatographed on silica gel, using dichloromethane/methanol (50:1) as eluent. The product fractions were combined and evaporated, and the residue was crystallized from ether to give the title compound (2.15 g), m.p. 188°-190° C. Found: C,59.62; H,4.43; N,9.26. C15 H13 BrN2 requires: C,59.82; H,4.35; N,9.30percent.

References: [1]Tetrahedron Letters,1993,vol. 34,p. 1529 - 1532.
[2]Patent: US5744488,1998,A .

5
[ 1075-34-9 ]
[ 99847-70-8 ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 14264 - 14265.
[2]Tetrahedron Letters,1993,vol. 34,p. 1529 - 1532.

6
5-bromo-2-methyl-3-(phenylthio)-1H-indole [ No CAS ]
[ 1075-34-9 ]

References: [1]Journal of Organic Chemistry,1994,vol. 59,p. 6372 - 6377.

7
[ 1075-34-9 ]
[ 98-09-9 ]
[ 181299-26-3 ]

Yield	Reaction Conditions	Operation in experiment
68.4%	With hydrogen; sodium hydride; In DMF (N,N-dimethyl-formamide); for 0.166667h;	To a solution OF 5-BROMO-2-METHYL-LH-INDOLE (1.5 g, 7.14 mmol) in 10 mL OF DMF was added 60percent sodium hydride in mineral oil (189 mg, 7.9 mmol). Once hydrogen gas evolution ceased, the mixture stirred for 10 minutes and was then treated with 1 RNL (7.83 mmol) of benzene sulfonyl chloride. The reaction was monitored by TLC (ethyl acetate-hexanes (5: 95) ) to afford a major new slightly less polar product than starting material. After 2 hours, the mixture was poured into 50 ML of saturated aqueous ammonium chloride solution and extracted with three 50 mL portions of ethyl acetate. The combined organic layers were washed with four 25 mL portions of brine, dried over magnesium sulfate, treated with activated carbon (NORIT AT"), filtered through diatomaceous earth, and concentrated in vacuo. The residue was adsorbed onto silica gel and chromatographed on silica gel using ethyl acetate-hexanes (1 : 99, then 2: 98, then 3: 97) to afford 1.71 g (68.4percent yield) of 1-BENZENESULFONYL-5-BROMO-2-METHYL-LH-INDOLE as a clear oil. To a chilled solution of L-BENZENESULFONYL-5-BROMO-2-METHYL-LII-INDOLE (350 mg, 0.99 mmol) in 4 mL of THF was added 440 PL (1.10 mmol) of N-BULI (2.5 M solution in hexanes), followed by dimethyl disulfide (100 PL, 1. 11 mmol). The mixture was stirred as it warmed to room temperature and was then quenched with ammonium chloride and extracted with three 15 ML portions of ethyl acetate. The combined organic layers were washed with three 15 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was adsorbed onto silica gel and chromatographed on silica gel using ethyl acetate- hexanes (1: 99, then 2: 98) to afford 156 mg (44.3percent yield) of 1-benzenesulfonyl-2-methyl-5- METHYLSULFANYL-LH-INDOLE as a clear oil. To a solution of L-BENZENESULFONYL-2-METHYL-5-METHYLSULFANYL-LH-INDOLE (156 mg, 0.49 mmol) in 10 mL of ethanol was added 10 mL of 10percent aqueous sodium hydroxide solution. The mixture was warmed at reflux for 18 hours. The mixture was then diluted with 10 mL of brine and extracted with three 20 mL portions of ethyl acetate. The combined organic layers were washed with two 10 mL portions of 10percent aqueous sodium hydroxide solution, two 20 ML portions of saturated aqueous ammonium chloride, two 20 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product was adsorbed onto silica gel and chromatographed on silica gel using ethyl acetate-hexanes (1: 99, then 2: 98, then 3: 97, then 5: 96) to afford 62 mg (71.2percent yield) OF 2-METHYL-5-METHYLSULFANYL-LH-INDOLE

References: [1]Synthetic Communications,1996,vol. 26,p. 3267 - 3276.
[2]Patent: WO2005/30213,2005,A1 .Location in patent: Page/Page column 192-193.

8
[ 6872-06-6 ]
[ 1075-34-9 ]

References: [1]Synthetic Communications,1996,vol. 26,p. 3267 - 3276.

9
[ 1075-34-9 ]
[ 83636-46-8 ]
[ 236747-79-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 307 - 312.

11
[ 5391-39-9 ]
[ 1075-34-9 ]
[ 227801-59-4 ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 5187 - 5189.
[2]Patent: EP1266897,2002,A2 .Location in patent: Page 91.

12
[ 1075-34-9 ]
[ 79-37-8 ]
(5-bromo-2-methyl-1H-indol-3-yl)-oxo-acetyl chloride [ No CAS ]

References: [1]Organic Letters,2002,vol. 4,p. 4033 - 4035.
[2]Organic Letters,2012,vol. 14,p. 4525 - 4527.

13
[ 1075-34-9 ]
[ 152431-65-7 ]
[ 74-88-4 ]
[ 765936-90-1 ]

References: [1]Molecular Crystals and Liquid Crystals,2005,vol. 430,p. 173 - 179.

14
[ 1075-34-9 ]
[ 105-36-2 ]
[ 72016-68-3 ]