685892-23-3|Methyl 2-bromo-6-chlorobenzoate| Ambeed

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Quality Control of [ 685892-23-3 ] Purity: 95% SDS Specification

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Product Details of [ 685892-23-3 ]

CAS No. :	685892-23-3
Formula :	C₈H₆BrClO₂
M.W :	249.49
SMILES Code :	O=C(OC)C1=C(Cl)C=CC=C1Br
MDL No. :	MFCD03789160
InChI Key :	XSNZTSBNXMQBRI-UHFFFAOYSA-N
Pubchem ID :	2759827

Safety of [ 685892-23-3 ]

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

Computational Chemistry of [ 685892-23-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	50.43
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	26.3 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.35
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	1.98
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.89
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.	3.24
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	3.01
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.69

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.87
Solubility	0.335 mg/ml ; 0.00134 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.	-2.16
Solubility	1.73 mg/ml ; 0.00695 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	-3.95
Solubility	0.0282 mg/ml ; 0.000113 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.	-6.42 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	0.0
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)	1.69

Application In Synthesis of [ 685892-23-3 ]

* 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 [ 685892-23-3 ]

[ 685892-23-3 ] Synthesis Path-Downstream 1~35

1
[ 81-46-9 ]
[ 685892-23-3 ]
2-(4-benzoylamino-9,10-dioxo-9,10-dihydro-[1]anthrylamino)-6-chloro-benzoic acid methyl ester [ No CAS ]

References: [1]Patent: DE652773,1936, .
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 24,p. 871.

2
[ 81-46-9 ]
[ 685892-23-3 ]
<i>N</i>-(9-chloro-5,8,14-trioxo-5,8,13,14-tetrahydro-naphth[2,3-<i>c</i>]acridin-6-yl)-benzamide [ No CAS ]

References: [1]Patent: DE652773,1936, .
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 24,p. 871.

3
[ 685892-23-3 ]
[ 656237-79-5 ]
4'-[(R)-1-(3-Amino-4-chloro-pyridin-2-ylamino)-ethyl]-3-chloro-biphenyl-2-carboxylic acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 6439 - 6442.

4
[ 592-31-4 ]
[ 685892-23-3 ]
3-butyl-5-chloroquinazoline-2,4(1H,3H)-dione [ No CAS ]

References: [1]Organic Letters,2006,vol. 8,p. 5089 - 5091.

5
[ 845829-93-8 ]
[ 685892-23-3 ]
[ 1048975-24-1 ]

Yield	Reaction Conditions	Operation in experiment
58%	With potassium carbonate;palladium diacetate; tris-(o-tolyl)phosphine; In tetrahydrofuran; water; at 20℃;	Intermediate 4; 4'-{(R)-1-[(3-Amino-oxetane-3-carbonyl)-amino]-ethyl}-3-chloro-3'-fluoro-biphenyl-2-carboxylic acid methyl ester Step A: 4'-((R)-1-tert-Butoxycarbonylamino-ethyl)-3-chloro-3'-fluoro-biphenyl-2-carboxylic acid methyl ester A mixture of {(R)-1-[2-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl}-carbamic acid tert-butyl ester (600 mg, 1.64 mmol, intermediate 13), <strong>[685892-23-3]methyl 2-bromo-6-chlorobenzoate</strong> (430 mg, 1.72 mmol) [CAS 685892-23-3; commercially available], tri-o-tolyl-phosphane (100 mg, 329 mumol), potassium carbonate (568 mg, 4.11 mmol) and palladium(II) acetate (18.4 mg, 82.1 mumol) in THF (20.0 ml) and water (1.18 ml) was stirred at room temperature over night. The reaction mixture was diluted with water and extracted three times with EtOAc. The combined extracts were washed with water and brine, dried with Na2SO4 and concentrated in vacuo. The remaining residue was purified by chromatography (silica gel; DCM/EtOAc 100:0-90:10) and the title compound was obtained as colorless oil (385 mg, 58%). MS: 466.1 [M-H+OAc]-.
58%	With potassium carbonate; tris-(o-tolyl)phosphine;palladium diacetate; In tetrahydrofuran; water; at 20℃;	Step A: 4'-((R)- l-tert-Butoxycarbonylamino-ethyl)-3-chloro-3'-fluoro-biphicarboxylic acid methyl ester A mixture of {(R)-l-[2-fluoro-4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-phenyl]- ethylj-carbamic acid tert-butyl ester (600 mg, 1.64 mmol, intermediate 13), methyl 2- bromo-6-chlorobenzoate (430 mg, 1.72 mmol) [CAS 685892-23-3; commercially available], tri-o-tolyl-phosphane (100 mg, 329 muiotaetaomicron), potassium carbonate (568 mg, 4.11 mmol) and palladium(II) acetate (18.4 mg, 82.1 muiotaetaomicron) in THF (20.0 ml) and water (1.18ml) was stirred at room temperature over night. The reaction mixture was diluted with water and extracted three times with EtOAc. The combined extracts were washed with water and brine, dried with Na2S04 and concentrated in vacuo. The remaining residue was purified by chromatography (silica gel; DCM / EtOAc 100:0-90: 10) and the title compound was obtained as colorless oil (385 mg, 58%). MS: 466.1 [M-H+OAc]".

References: [1]Patent: US2012/165338,2012,A1 .Location in patent: Page/Page column 17.
[2]Patent: WO2012/89601,2012,A1 .Location in patent: Page/Page column 42-43.
[3]Journal of Medicinal Chemistry,2007,vol. 50,p. 272 - 282.

6
C₁₇H₂₈BFN₂O₃S [ No CAS ]
[ 685892-23-3 ]
[ 943975-48-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3608 - 3612.

7
[ 685892-23-3 ]
[ 943975-64-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3608 - 3612.

8
[ 685892-23-3 ]
C₂₁H₁₈ClF₄N₃O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3608 - 3612.

9
[ 93224-85-2 ]
[ 18107-18-1 ]
[ 685892-23-3 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol;	To a solution of 2-bromo-6-chlorobenzoic acid (17.7 g, 75.2 mmol) in methanol (200 mL) at 0 C. was added (trimethylsilyl)diazomethane (2M in hexanes, 100 mL, 0.200 mol). The solution was stirred at 0 C. for 1.5 hours, then warmed to room temperature and washed with aqueous sodium bicarbonate and brine, dried over Na2SO4, filtered and concentrated. The residue was subjected to silica gel chromatography eluted with 0-5% ethyl acetate in hexanes to provide methyl 2-bromo-6-chlorobenzoate as a pale yellow oil that gave proton NMR spectra consistent with theory.

References: [1]Patent: US2003/220375,2003,A1 .

10
tert-butyl (1R)-1-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxa-borolan-2-yl)phenyl]ethylcarbonate [ No CAS ]
[ 685892-23-3 ]
[ 6163-58-2 ]
[ 1048975-24-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;palladium diacetate; In tetrahydrofuran; water; ethyl acetate;	A mixture of <strong>[685892-23-3]methyl 2-bromo-6-chlorobenzoate</strong> (2.25 g, 9.03 mmol), tert-butyl (1R)-1-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-ethylcarbonate (see Example 11, 3.00 g, 8.21 mmol), potassium carbonate (2.84 g, 20.5 mmol), tri-o-tolylphosphine (0.10 g, 0.33 mmol), and palladium acetate (0.018 g, 0.08 mmol) in 40 mL of THF and 4 mL of water was heated in a sealed flask at 100 C. for 4 h. The mixture was then cooled and concentrated in vacuo. The resulting residue was dissolved in ethyl acetate, washed with water and brine, dried over Na2SO4, filtered and concentrated under vacuum. The residue was subjected to silica gel chromatography eluted with 0-10% ethyl acetate and hexane to provide methyl 4'-{(1R)-1-[(tert-butoxycarbonyl)amino]ethyl}-3-chloro-3'-fluoro-1,1'-biphenyl-2-carboxylate that gave proton NMR spectra consistent with theory.

References: [1]Patent: US2003/220375,2003,A1 .

11
[ 89466-08-0 ]
[ 685892-23-3 ]
7-chloro-6H-benzo[c]chromen-6-one [ No CAS ]

References: [1]Journal of Combinatorial Chemistry,2010,vol. 12,p. 664 - 669.

12
[ 93224-85-2 ]
[ 77-78-1 ]
[ 685892-23-3 ]

Yield	Reaction Conditions	Operation in experiment
75%		LiOH.H20 (180 mg, 4.24 mmol) was added to a solution of 2-bromo-6-chlorobenzoic acid (i-la) (1.0 g, 4.24 mmol) in THF (30 ml). The mixture was stirred at 25 C for lh. Then the Me2S04 (1.1 g, 8.48 mmol) was added to the reaction mixture. The mixture was warmed to 85 C and stirred at 85 C for 21 h. After cooled, H3.H20 was added dropwise to the mixture until pH=7-8. The solution was poured into water and THF was evaporated. The water layer was extracted with EA (60 ml). The organic layer was dried over Na2S04 and concentrated to obtain 800 mg (75%) of the title compound. LCMS (ESI): calc'd for C8H6BrC102 [M+H]+: 251, found: 251.

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7232 - 7246.
[2]Patent: WO2014/26327,2014,A1 .Location in patent: Page/Page column 52.

13
[ 685892-23-3 ]
[ 1338224-15-9 ]