[ CAS No. 936092-87-4 ] {[proInfo.proName]}

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Quality Control of [ 936092-87-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 936092-87-4 ]

SDS Specification

Alternatived Products of [ 936092-87-4 ]

Product Details of [ 936092-87-4 ]

CAS No. :	936092-87-4	MDL No. :	MFCD08272256
Formula :	C₉H₈BrN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FEMJIOSKNKIMBM-UHFFFAOYSA-N
M.W :	210.07	Pubchem ID :	24729279
Synonyms :		Chemical Name :	4-Bromo-7-methyl-1H-indole

Calculated chemistry of [ 936092-87-4 ] Expand+

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 ?2

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) :	2.09
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 :	2.94

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 :	1.42

Safety of [ 936092-87-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280	UN#:	N/A
Hazard Statements:	H302-H317	Packing Group:	N/A
GHS Pictogram:

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 1~14

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).

Reference： [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

2
[ 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).

Reference： [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)+.

Reference： [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)+.

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

5
[ 936092-87-4 ]
[ 1101818-09-0 ]
[ 1426154-19-9 ]