845751-59-9|7-Bromo-2H-indazole| Ambeed

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Quality Control of [ 845751-59-9 ] Purity: 97% SDS Specification

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Product Details of [ 845751-59-9 ]

CAS No. :	845751-59-9
Formula :	C₇H₅BrN₂
M.W :	197.03
SMILES Code :	BrC1=CC=CC2=CNN=C12
MDL No. :	MFCD23134611
InChI Key :	KMHHWCPTROQUFM-UHFFFAOYSA-N
Pubchem ID :	20323899

Safety of [ 845751-59-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 845751-59-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	43.79
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	28.68 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.33
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	2.24
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.33
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.	1.88
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	2.75
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.11

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.14
Solubility	0.143 mg/ml ; 0.000726 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.	-2.48
Solubility	0.656 mg/ml ; 0.00333 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	-3.77
Solubility	0.0337 mg/ml ; 0.000171 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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.	-5.91 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)	1.47

Application In Synthesis of [ 845751-59-9 ]

* 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 [ 845751-59-9 ]

[ 845751-59-9 ] Synthesis Path-Downstream 1~28

1
[ 845751-60-2 ]
[ 845751-59-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium tert-butylate; In dimethyl sulfoxide; at 20.0℃; for 2h;	A solution of (2-bromo-6-methylphenylazo)-t-butylsulfide (2b; 880 mg, 3.06 mmol) in 10 mL dry DMSO was added dropwise to a solution of potassium t-butoxide (3.44 g, 30.6 mmol) in 25 mL dry DMSO under Ar. The reaction mixture was stirred at room temp for 2 hr, then poured into 150 g ice and 150 mL 2 N HCl solution. The mixture was extracted with ether (2?150 mL). The combined ethereal extracts were washed with brine and dried over MgSO4. Evaporation of the solvent afforded 581 mg (96%) of 3 as a beige solid.
96%	With potassium tert-butylate; In dimethyl sulfoxide; at 20.0℃; for 2h;	step 4 7-Bromoindazole (3) -A solution of (2-bromo-6-methylphenylazo)-t-butylsulfide (2b; 880 mg, 3.06 mmol) in 10 mL dry DMSO was added dropwise to a solution of potassium t-butoxide (3.44 g, 30.6 mmol) in 25 mL dry DMSO under Ar. The reaction mixture was stirred at room temperature for 2 hr, and then poured into 150 g ice and 150 mL 2 N HC1 solution. The mixture was extracted with ether (2 x 150ML). The combined ethereal extracts were washed with brine and dried over MGS04. Evaporation of the solvent afforded 581 mg (96%) of 3 as a beige solid.

References: [1]Patent: US2004/110815,2004,A1 .Location in patent: Page/Page column 19.
[2]Patent: WO2005/16892,2005,A1 .Location in patent: Page/Page column 69.
[3]Journal of Medicinal Chemistry,2012,vol. 55,p. 9089 - 9106,18.

2
[ 845751-59-9 ]
[ 77-78-1 ]
[ 701910-14-7 ]
7-bromo-1-methyl-1H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%		A mixture of <strong>[845751-59-9]7-bromoindazole</strong> (3; 576 mg, 2.92 mmol) and NaOH (510 mg, 12.7 mmol) in 15 mL H2O were heated in an oil bath under N2 atmosphere until the solids dissolved and the resulting solution was cooled to 65 C. Dimethyl sulfate (0.78 mL, 1.03 g, 8.18 mmol) was added and the mixture stirred at 65 for 2 hr. The reaction mixture was cooled to rt and extracted with CH2Cl2 (2×50 mL). The combined CH2Cl2 extracts were washed with brine and dried over Na2SO4. Evaporation ofthe solvent afforded 775 mg of a mixture of 1-methyl- and 2-methy-<strong>[845751-59-9]7-bromoindazole</strong>s which were separated by flash chromatography on SiO2 using EtOAc:hexane (1:2) which afforded 251 mg (45%) of 7-bromo-2-methylindazole (4).

References: [1]Patent: US2004/110815,2004,A1 .Location in patent: Page/Page column 19.

3
[ 845751-59-9 ]
[ 68716-47-2 ]
[ 845751-61-3 ]

Yield	Reaction Conditions	Operation in experiment
83%		EXAMPLE 2 7- (2,4-Dichloro-phenyl)-2-methyl-2H-indazole 5 : Ar = 2,4-dichlorophenyl ; R = Me step 1 A solution OF 7-BROMO-LH-INDAZOLE (3; 1.01 g, 5.13 mmol) and tetrakis (triphenylphosphine) palladium (0) (0.176 g, 0.152 mmol) in 15 mL of ethylene glycol dimethyl ether was stirred for 30 m. To the solution was added 2,4-dichlorophenyl boronic acid (1.93 g, 10.1 mmol) and a 2 M aqueous NA2CO3 solution (7.1 mL, 14.2 mmol). The orange-yellow mixture was stirred at 80 C for 19 h, allowed to cool, and then partitioned between 50 mL of ethyl acetate and 50 mL of water. The organic layer was dried over MGS04, filtered, and concentrated to an orange oil. Column chromatography (0O10% EtOAc/hexanes) afforded OF 7-(2, 4-DICHLORO-PHENYL)-LH- indazole as a pale yellow foamy solid (4; 1.12 g, 83%).

References: [1]Patent: WO2005/16892,2005,A1 .Location in patent: Page/Page column 69.

4
[ 53848-17-2 ]
[ 845751-59-9 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9089 - 9106,18.
[2]Patent: WO2005/16892,2005,A1 .

5
[ 845751-59-9 ]
[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]-(2-butyl-2H-indazol-7-yl)amine hydrochloride [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9089 - 9106,18.

6
[ 845751-59-9 ]
[ 77-78-1 ]
[ 701910-14-7 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9089 - 9106,18.

7
[ 845751-59-9 ]
[ 625-22-9 ]
[ 1259032-97-7 ]