165669-07-8|7-Bromo-4-methyl-1H-indole| Ambeed

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 165669-07-8 ] Purity: 97% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 165669-07-8 ]

CAS No. :	165669-07-8
Formula :	C₉H₈BrN
M.W :	210.07
SMILES Code :	CC1=CC=C(Br)C2=C1C=CN2
MDL No. :	MFCD09955320
InChI Key :	SJOBFYZCJCKOAF-UHFFFAOYSA-N
Pubchem ID :	18752862

Safety of [ 165669-07-8 ]

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

Computational Chemistry of [ 165669-07-8 ] 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	3.1
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	2.95

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	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.	-5.38 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)	1.36

Application In Synthesis of [ 165669-07-8 ]

* 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 [ 165669-07-8 ]

[ 165669-07-8 ] Synthesis Path-Downstream 1~20

1
[ 5326-34-1 ]
[ 1826-67-1 ]
[ 165669-07-8 ]

Yield	Reaction Conditions	Operation in experiment
42%	In tetrahydrofuran; at -60 - -30℃; for 1h;Inert atmosphere;	To a solution of 1-bromo-4-methyl-2-nitro-benzene (40.0 g, 185 mmol, 25.3 mL) in tetrahydrofuran (400 mL) was added bromo(vinyl)magnesium (1 M, 611 mL) at -60 OC under nitrogen gas atmosphere. The reaction mixture was then stirred at -30 OC for 1 hour. On completion, the reaction mixture was quenched with saturated ammonium chloride solution (150 mL), followed with water (100 mL). The mixture was concentrated in vacuo to remove the tetrahydrofuran. The residue was extracted with ethyl acetate (2×500 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was then purified by column chromatography (petroleum ether:ethyl acetate=100:1) to give the title compound (18.0 g, 42% yield) as a yellow oil. 1H NMR (400 MHz, DMSO-d6) delta 11.27 (br s, 1H), 7.37 (t, J=2.8 Hz, 1H), 7.18 (d, J=7.6 Hz, 1H), 6.75 (dd, J=0.8, 7.6 Hz, 1H), 6.57 (dd, J=1.6, 3.2 Hz, 1H), 2.44 (s, 3H).
	With ammonium chloride; In tetrahydrofuran; ethyl acetate;	Production Example 7 7-Bromo-4-methyl-1H-indole To 300 ml of a solution of 65.0 g (301 mmol) of 2-bromo-5-methylnitrobenzene in tetrahydrofuran was added 1 liter of a 1.0M solution of vinyl magnesium bromide (1 mol) in tetrahydrofuran at -60 C. in a nitrogen atmosphere under stirring during 1 hour. To the reaction mixed solution were added a saturated aqueous solution of ammonium chloride and ethyl acetate, and the resulting insoluble matters were filtered off. The resulting filtrate was dried over magnesium sulfate, concentrated, and then the resulting residue was purified by a silica gel column chromatography to give 35.5 g of the title compound. 1H-NMR(DMSO-d6) delta (ppm); 2.42(3H,s), 6.55(1H,s) 6.73(1H,d,J=7.6 Hz), 7.16(1H,d,J=7.6 Hz), 7.35(1H,s), 1 11.24(1H,brs)
	With ammonium chloride; In tetrahydrofuran; ethyl acetate;	PRODUCTION EXAMPLE 7 7-Bromo-4-methyl-1H-indole 1 l (1 mol) of a tetrahydrofuran solution containing 1.0 M vinylmagnesium bromide was added to a tetrahydrofuran solution (300 ml) containing 65.0 g (301 mmol) of 2-bromo-5-methylnitrobenzene at -60 C. under stirring for one hour in nitrogen atmosphere. An aqueous saturated ammonium chloride and ethyl acetate were added to the reaction mixture solution, and the insoluble matters were filtered off. The filtrate was dried over magnesium sulfate and concentrated. Then, the residue was purified by silica gel column chromatography, to give 35.5 g of the title compound. 1H-NMR(DMSO-d6) delta (ppm): 2.42(3H, s), 6.55(1H, s), 6.73(1H, d, J=7.6 Hz), 7.16(1H, d, J=7.6 Hz), 7.35(1H, s), 11.24(1H, br s)

In tetrahydrofuran; at -50℃; for 1.5h;

(4-methyl-1 H-indol-7-yl)(phenyl)methanamine - To a solution of 1 -bromo-4-methyl-2-nitrobenzene (2.0 g, 9.26 mmol) in THF was added vinyl magnesium bromide 1 M in THF (27.8 ml_, 27.77 mmol) at - 50C. The reaction was finished after 1 h30. The reaction was quenched with sat. NH4CI. The aqueous layer was extracted with a non-water miscible organic solvent. The combined organic layers were dried over MgS04, filtered and the solution was concentrated to dryness. The crude material was purified on silica gel column chromatography usinf hexanes/EtOAc (9:1 ) as eluent. A solution of the freshly synthesized 7-bromo-4-methyl-1 H-indole (1 .1 g, 5.24 mmol), zinc cyanide (860 mg, 7.32 mmol) and Pd(PPh3)4 (0.03 eq.) in DMF Ex.97 was heated under microwave irradiation at 170C for 1 h. After cooling, water was added to quench the reaction. The aqueous layer was extracted with a non-water miscible organic solvent. The combined organic layers were dried over MgS04, filtered and the solution was concentrated under reduced pressure. The crude material was purified on silica gel column chromatography using hexanes/EtOAc (12:1 to 4:1 ) as eluent. The titled compound was then obtained following the modified procedure described in WO2006035157 (Protocol A) - Yield: 2% ; appearance: pale brown solid ; 1 H NMR, d (ppm) (Methanol d4) : 2.49 (s, 3H); 5.51 (s, 1 H); 6.47 (d, 1 H, J=3.2Hz); 6.81 (dd, 1 H, J=0.6Hz , J=7.3Hz); 7.01 (d, 1 H, J=7.3Hz); 7.17-7.22 (m, 2H); 7.25-7.31 (m, 2H); 7.39- 7.43 (m, 2H)

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 638 - 641.
[2]Patent: US2019/192668,2019,A1 .Location in patent: Paragraph 2467; 2468.
[3]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1223 - 1226.
[4]Patent: US2002/128480,2002,A1 .
[5]Patent: US2004/18192,2004,A1 .
[6]Patent: WO2016/102633,2016,A1 .Location in patent: Page/Page column 63.

2
[ 165669-07-8 ]
7-azido-4-methyl-1<i>H</i>-indole [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1223 - 1226.

3
[ 165669-07-8 ]
[ 16096-32-5 ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 638 - 641.

4
[ 165669-07-8 ]
[ 292636-15-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1223 - 1226.

5
[ 165669-07-8 ]
[ 292636-24-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1223 - 1226.

6
[ 165669-07-8 ]
4-Amino-N-(3-chloro-4-methyl-1H-indol-7-yl)-benzenesulfonamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1223 - 1226.

7
[ 165669-07-8 ]
[ 292636-20-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1223 - 1226.

8
[ 165669-07-8 ]
4-Methyl-1H-indole-7-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; carbon dioxide; In tetrahydrofuran; hexane; water;	Production Example 8 4-Methyl-1H-indole-7-carboxylic Acid To a solution (200 ml) of 35.5 g (169 mmol) of the compound of Production Example 7 in tetrahydrofuran was added a 1.6M solution (350 ml) of butyl lithium (384 mmol) in hexane in a nitrogen atmosphere at -78 C. under stirring. After stirring for 40 minutes under ice-cooling, carbon dioxide was introduced to the reaction solution at -50 C. and stirred as it was for 15 minutes. Water was added to the reaction mixture at the same temperature, the solvent was evaporated and the resulting precipitates were collected by filtration and washed with water. The precipitates were dissolved in 300 ml of tetrahydrofuran, dried over magnesium sulfate and then concentrated to dryness to give 25.9 g of the title compound. 1H-NMR (DMSO-d6) delta (ppm); 2.51 (3H, s), 6.53 (1H, s), 6.88(1H,d,J=7.6 Hz), 7.31(1H,s), 7.62(1H,d,J=7.6 Hz), 10.99(1H,brs), 12.79(1H,brs).

References: [1]Patent: US2002/128480,2002,A1 .

Yield	Reaction Conditions	Operation in experiment
		PREPARATIVE EXAMPLE 3 STR15 N-Chlorosuccinimide (4.0 g, 30.0 mmol) was added to 250 ml of an acetonitrile solution of 5.8 g (27.6 mmol) of 7-bromo-4-methyl-1H-indole prepared from 2-bromo-5-methylnitrobenzene in a similar manner to that of Preparative Example 1.
		Production Example 7 7-Bromo-4-methyl-1H-indole 1 1 (1 mol) of a tetrahydrofuran solution containing 1.0 M vinylmagnesium bromide was added to a tetrahydrofuran solution (300 ml) containing 65.0 g (301 mmol) of 2-bromo-5-methylnitrobenzeneat -60C under stirring for one hour in nitrogen atmosphere. An aqueous saturated ammonium chloride and ethyl acetate were added to the reaction mixture solution, and the insoluble matters were filtered off. The filtrate was dried over magnesium sulfate and concentrated. Then, the residue was purified by silica gel column chromatography, to give 35.5 g of the title compound. 1H-NMR(DMSO-d6) delta (ppm): 2.42(3H, s), 6.55(1H, s), 6.73(1H, d, J=7.6Hz), 7.16(1H, d, J=7.6Hz), 7.35(1H, s), 11.24(1H, br s)

10
[ 557-21-1 ]
[ 165669-07-8 ]
C₁₀H₈N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 170℃; for 1h;Microwave irradiation;	(4-methyl-1 H-indol-7-yl)(phenyl)methanamine - To a solution of 1 -bromo-4-methyl-2-nitrobenzene (2.0 g, 9.26 mmol) in THF was added vinyl magnesium bromide 1 M in THF (27.8 ml_, 27.77 mmol) at - 50C. The reaction was finished after 1 h30. The reaction was quenched with sat. NH4CI. The aqueous layer was extracted with a non-water miscible organic solvent. The combined organic layers were dried over MgS04, filtered and the solution was concentrated to dryness. The crude material was purified on silica gel column chromatography usinf hexanes/EtOAc (9:1 ) as eluent. A solution of the freshly synthesized 7-bromo-4-methyl-1 H-indole (1 .1 g, 5.24 mmol), zinc cyanide (860 mg, 7.32 mmol) and Pd(PPh3)4 (0.03 eq.) in DMF Ex.97 was heated under microwave irradiation at 170C for 1 h. After cooling, water was added to quench the reaction. The aqueous layer was extracted with a non-water miscible organic solvent. The combined organic layers were dried over MgS04, filtered and the solution was concentrated under reduced pressure. The crude material was purified on silica gel column chromatography using hexanes/EtOAc (12:1 to 4:1 ) as eluent. The titled compound was then obtained following the modified procedure described in WO2006035157 (Protocol A) - Yield: 2% ; appearance: pale brown solid ; 1 H NMR, d (ppm) (Methanol d4) : 2.49 (s, 3H); 5.51 (s, 1 H); 6.47 (d, 1 H, J=3.2Hz); 6.81 (dd, 1 H, J=0.6Hz , J=7.3Hz); 7.01 (d, 1 H, J=7.3Hz); 7.17-7.22 (m, 2H); 7.25-7.31 (m, 2H); 7.39- 7.43 (m, 2H)

References: [1]Patent: WO2016/102633,2016,A1 .Location in patent: Page/Page column 63.

11
[ 165669-07-8 ]
[ 289483-84-7 ]