936092-87-4|4-Bromo-7-methyl-1H-indole| Ambeed

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Quality Control of [ 936092-87-4 ] Purity: 95% SDS Specification

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Product Details of [ 936092-87-4 ]

CAS No. :	936092-87-4
Formula :	C₉H₈BrN
M.W :	210.07
SMILES Code :	CC1=CC=C(Br)C2=C1NC=C2
MDL No. :	MFCD08272256
InChI Key :	FEMJIOSKNKIMBM-UHFFFAOYSA-N
Pubchem ID :	24729279

Safety of [ 936092-87-4 ]

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

Computational Chemistry of [ 936092-87-4 ] 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.	2.09
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	2.94

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)	1.42

Application In Synthesis of [ 936092-87-4 ]

* 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 [ 936092-87-4 ]

[ 936092-87-4 ] Synthesis Path-Downstream 1~18

1
[ 60956-26-5 ]
[ 1826-67-1 ]
[ 936092-87-4 ]

Yield	Reaction Conditions	Operation in experiment
43%	In tetrahydrofuran; at -40℃; for 0.666667h;Inert atmosphere;	A solution of 4-bromo-1 -methyl-2-nitrobenzene (1 1 .57 mmol, 2.5 g) in THF (1 16 mL) under nitrogen atmosphere was cooled to -40 5C and vinylmagnesium bromide (46.28 mmol, 46 mL) was added. The reaction mixture was stirred for 40 min and quenched with saturated aqueous NH4CI. The aqueous layer was extracted with ethyl acetate twice and the combined organic layers were dry with Na2S04, filtered and concentrated. The crude product thus obtained was dissolved in THF (35 mL) and cooled to 0 5C. 0.5 N HCI (4.4 mL) was added and the reaction mixture stirred at 05C for 1 h, when it was quenched with NaHC03 (44 mL). The aqueous layer was extracted with ethyl acetate twice and the combined organic extracts were dried with Na2S04, filtered and concentrated. Purification of the crude material by flash chromatography on silica gel using an elution of 1 1 % ethyl acetate in hexanes afforded the pure title compound (1 .05 g. Yield: 43%) 1 H NMR (400 MHz, CDCI3) δ 8.21 (1 H, brs), 7.28-7.26 (1 H, m), 7.21 (1 H, d, J = 7.2 Hz), 6.87 (1 H, d, J = 6.8 Hz), 6.63-6.61 (1 H, m), 2.47 (3H, s). LC-MS: tR = 3.58 [M+H]+=not ion (method 3)
43%		A solution of 4-bromo-1-methyl-2-nitrobenzene (11.57 mmol, 2.5 g) in THF (116 mL) under nitrogen atmosphere was cooled to -40 C and vinyl magnesium bromide (46.28 mmol, 46 mL) was added. The reaction mixture was stirred for 40 min and quenched with saturated aqueous NH4Cl. The aqueous layer was extracted with ethyl acetate twice and the combined organic layers were dried with Na2SO4, filtered and concentrated. The crude product thus obtained was dissolved in THF (35 mL) and cooled to 0 C. 0.5 N HCl (4.4 mL) was added and the reaction mixture was stirred at 0 C for 1 h, then it was quenched with NaHCO3 (44 mL). The aqueous layer was extracted with ethyl acetate twice and the combined organic extracts were dried with Na2SO4, filtered and concentrated. Purification of the crude material by flash chromatography over silica gel using an elution of 11% ethyl acetate in hexanes afforded 1.05 g (Yield: 43%) of the pure title compound 25. 1H NMR (400 MHz, CDCl3): δ 8.21 (1H, brs), 7.28-7.26 (1H, m), 7.21 (1H, d, J = 7.2 Hz), 6.87 (1H, d, J = 6.8 Hz), 6.63-6.61 (1H, m), 2.47 (3H, s).
		Example 6: 2-(7-MethvI-lH-indoI-4-vIV6-(4-methyl-piperazin-l-ylmethyI)-4- morpholin-4-yl-thienof3,2-dlpyrimidine; To a solution of 4-bromo-2-nitrotoluene (3.0 g, 13.9 mmol) in THF (40 mL) at-40 C was added vinyl magnesium bromide (48.6 mmol, 48.6 mL; 1.0 M in THF) dropwise over 15 minutes and the mixture stirred at -40 0C for 1.5 hours. The reaction was quenched by the addition of saturated aqueous ammonium chloride and extracted with ethyl acetate. The combined organic layers were washed with brine, 20 separated and dried (MgSO4). The residue was evaporated and purified by column chromatography to yield 4-bromo-7-methylindole (1.03 g).

References: [1]Patent: WO2013/149997,2013,A1 .Location in patent: Page/Page column 120-121.
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2016,vol. 55B,p. 1117 - 1130.
[3]Patent: WO2007/122410,2007,A1 .Location in patent: Page/Page column 93.

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[ 936092-87-4 ]
[ 73183-34-3 ]
[ 955979-09-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 80℃; for 8h;	To a suspension of 4-bromo-7-methylindole (349 mg, 1.66 mmol), bispinacolatodiboron (2.66 mmol, 674 mg) and potassium acetate (4.98 mmol, 489 mg) in DMSO (12 mL) was added Pd(dppf)2Cl2 (0.05 mmol, 41 mg). The mixture25 was degassed with argon and heated at 80 0C for 8 hours. The mixture was allowed to cool and partitioned between ether and water and the aqueous later extracted with ether. The combined organic layers were washed with brine, separated and dried. The crude product was purified by chromatography to yield 7-methyl-4-(4,4,5,5- tetramethyl-[l, 3,2]dioxaborolan-2-yl)-lH-indole as a' solid which was triturated in30 petrol giving a white crystalline solid (117 mg).

References: [1]Patent: WO2007/122410,2007,A1 .Location in patent: Page/Page column 93.

3
[ 936092-87-4 ]
[ 936092-52-3 ]
5-methyl-N₄-(7-methyl-1H-indol-4-yl)-N₂-(4-(4-methylpiperazin-1-yl)phenyl)pyrimidine-2,4-diamine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13%	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; for 20h;Heating / reflux;	[0242] A mixture of intermediate 32 (674 mg, 2.25 mmol), 4-bromo-7-methyl-lH-indole (522 mg, 2.48 mmol), Pd2(dba)3 (182 mg, 0.2 mmol), Xantphos (360 mg, 0.6 mmol) and cesium carbonate (2.6 g, 8 mmol) was suspended in dioxane (50 mL) and heated at reflux under the argon atmosphere for 20 h. The mixture was filtered and the filtrate concentrated in vacuo. The residue was purified by HPLC to afford the title compound (136 mg of HCl salt, 13%) as a white solid. <n="137"/>[0243] 1H NMR (500 MHz, DMSO-d6): δ 2.21 (s, 3H), 2.55 (s, 3H), 2.80 (d, J= 4.6 Hz, 3H), 3.00-3.05 (m, 2H), 3.10-3.16 (m, 2H), 3.45-3.48 (m, 2H), 3.64-3.66 (m, 2H), 6.33-6.34 (m, IH), 6.63 (br, 2H), 6.92-6.97 (m, 4H), 7.35 (t, J= 2.7 Hz, IH), 7.83 (s, IH), 10.04 (s, IH), 10.24 (s, IH), 11.08 (br s, IH), 11.34 (s, IH), 12.12 (br s, IH). MS (ES+): m/z 428 (M+H)+.

References: [1]Patent: WO2007/53452,2007,A1 .Location in patent: Page/Page column 135-136.

4
[ 936092-87-4 ]
[ 936092-38-5 ]
N₂-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)-5-methyl-N₄-(7-methyl-1H-indol-4-yl)pyrimidine-2,4-diamine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%		[0246] A mixture of intermediate 38 (410 mg, 1.3 mmol), 4-bromo-7-methyl-lH-indole (275 mg, 1.3 mmol), Pd2(dba)3 (92 mg, 0.1 mmol), Xantphos (180 mg, 0.3 mmol) and cesium carbonate (1.3 g, 4 mmol) was suspended in dioxane (50 mL) and heated at reflux under the argon atmosphere for 20 h. The mixture was filtered and the filtrate concentrated in vacuo. The residue was purified by HPLC to afford the title compound (92 mg of HCl salt, 15%) as a white solid.[0247] 1H NMR (500 MHz, DMSO-d6): δ 1.88-1.90 (m, 2H), 1.93-2.02 (m, 2H), 2.21 (s, 3H), 2.55 (s, 3H), 3.06-3.10 (m, 2H), 3.51-3.54 (m, 4H), 4.26 (t, J= 4.9 Hz, 2H), 6.33-6.34 (m, IH), 6.61 (br d, 2H), 6.93-6.95 (m, 2H), 7.03 (d, J= 8.9 Hz, 2H), 7.34 (t, J= 2.8 Hz, IH), 7.85 (s, IH), 10.07 (s, IH), 10.33 (s, IH), 10.91 (br s, IH), 11.34 (s, IH), 12.15 (br s, H). MS (ES+): m/z 443 (M+H)+.

References: [1]Patent: WO2007/53452,2007,A1 .Location in patent: Page/Page column 137.

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[ 1101818-09-0 ]
[ 1426154-19-9 ]