174603-55-5|3-(2-Bromo-4-fluorophenyl)propionic acid| Ambeed

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Quality Control of [ 174603-55-5 ] Purity: 97% SDS Specification

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Product Details of [ 174603-55-5 ]

CAS No. :	174603-55-5
Formula :	C₉H₈BrFO₂
M.W :	247.06
SMILES Code :	O=C(O)CCC1=CC=C(F)C=C1Br
MDL No. :	MFCD06656907
InChI Key :	VHFQIJJCQTZKFK-UHFFFAOYSA-N
Pubchem ID :	10922852

Safety of [ 174603-55-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 174603-55-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.22
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	50.45
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	37.3 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.84
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	2.47
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.03
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.	3.11
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	2.99
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.	-3.07
Solubility	0.21 mg/ml ; 0.000848 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.	-2.9
Solubility	0.313 mg/ml ; 0.00127 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	-3.72
Solubility	0.0473 mg/ml ; 0.000191 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.	-6.05 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.	0.56

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 [ 174603-55-5 ]

* 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 [ 174603-55-5 ]

[ 174603-55-5 ] Synthesis Path-Downstream 1~35

1
[ 174603-55-5 ]
3-(2-bromo-4-fluorophenyl)propionyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride; In dichloromethane; at 0 - 20℃; for 18h;	To a solution of <strong>[174603-55-5]3-(2-bromo-4-fluoro-phenyl)-propionic acid</strong> (5.6 g, 22.67 mmol) in 0H2012 (56 mL) was added oxalyl chloride (4.13 mL, 48.18 mmol) at 0 00 and allowed to stir atRT for 1 8h. Excess oxalyl chloride was removed in vacuo to give the acid chloride as a semi-solid. The acid chloride was dissolved in 0H2012 (30 mL) and added to a suspension of anhydrous AId3 (3.77 g, 28.340 mmol) in 0H2012 (60 mL) at 0 00 and the reaction mixture was heated under reflux for 2h. The reaction mixture was cooled to RT, poured into ice-water and extracted with 0H2012 (1 x 150 mL). The combined organiclayers were washed with 0.1 M sodium hydroxide solution and water. The organic layer was dried (Na2SO4) and concentrated in vacuo to afford 4-bromo-6-fluoro-indan-1-one as an off-white solid (4.1 g, 78%).Rt:0.5 (10% EtOAc/pet-ether).1H NMR (400MHz, 0D013): O 7.55-7.52 (m, 1H), 7.39-7.37 (m, 1H), 3.06-3.03 (m, 2H),2.79-2.76 (m, 2H).

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416.
[2]Patent: WO2015/36759,2015,A1 .Location in patent: Page/Page column 171.

2
[ 174603-54-4 ]
[ 174603-55-5 ]

Yield	Reaction Conditions	Operation in experiment
33%	With water; potassium hydroxide; for 4.5h;Reflux;	To a mixture of 2-(2-bromo-4-fluoro-benzyl)-malonic acid diethyl ester (2.1 g, 6.07 mmol)and water (14 mL) was added potassium hydroxide (0.68 g, 12.14 mmol) and the reactionmixture was heated under reflux for 4.5h. The reaction mixture was cooled to RT and theethanol removed in vacuo. The aqueous residue was cooled to 0 00, acidified with conc.H2S04, and heated at 120 00 for 16h. The reaction mixture was cooled to 0 00 theprecipitated solid was collected by filtration, washed with water and dried to obtain 3-(2-bromo-4-fluoro-phenyl)-propionic acid as an off-white solid (0.5 g, 33%).R: 0.2 (30% EtOAc/pet-ether).1H NMR (400MHz, DMSO-d6): O 12.26 (5, 1H), 7.55-7.52 (m, 1H), 7.42-7.38 (m, 1H),7.23-7.18 (m, 1H), 2.90 (t, J= 7.8 Hz, 2H), 2.52 (t, J= 7.8 Hz, 2H).

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416.
[2]Patent: WO2015/36759,2015,A1 .Location in patent: Page/Page column 171.

3
[ 1422-53-3 ]
[ 174603-55-5 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416.

4
[ 61150-57-0 ]
[ 174603-55-5 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416.
[2]Patent: WO2015/36759,2015,A1 .

5
[ 174603-55-5 ]
[ 174603-56-6 ]

Yield	Reaction Conditions	Operation in experiment
970 mg	In trifluorormethanesulfonic acid; at 60 - 80℃; for 18h;Inert atmosphere;	Under argon <strong>[174603-55-5]3-(2-bromo-4-fluorophenyl)propanoic acid</strong> (1 .2 g) is added in small portions to trifluoromethanesulfonic acid (15 mL) at room temperature. The mixture is stirred for 2 hours at 60C and for 16 hours at 80C. After cooling to room temperature the mixture is poured slowly in ice-water. The aqueous phase is extracted twice with ethyl acetate. The combined organic phases are washed with saturated aqueous Na2CO3 solution and brine. After drying (MgSO4) the solvent is evaporated. The residue is stirred with dichloromethane (40 ml_), filtered and washed with dichloromethane. The combined dichloromethane phases are concentrated to give the title compound. Yield: 970 mg; LC (method 3): tR = 0.60 min; Mass spectrum (ESI+): m/z = 229 [M+H]+.

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416.
[2]Patent: WO2013/144098,2013,A1 .Location in patent: Page/Page column 114; 115.
[3]Patent: WO2015/36759,2015,A1 .

6
[ 174603-55-5 ]
[ 174603-60-2 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416.

7
[ 174603-55-5 ]
(E)-2-(4-bromo-6-fluoro-1-indanylidene)acetamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416.

8
[ 174603-55-5 ]
[ 174603-59-9 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416.

9
[ 174603-55-5 ]
[ 174603-58-8 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416.

10
[ 174603-55-5 ]
[ 174603-57-7 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416.

Yield	Reaction Conditions	Operation in experiment
20.6 g (91%)		c) Preparation of 3-(2-Bromo-4-Fluorophenyl) Propionic Acid A mixture of diethyl 2-(2-bromo-4-fluorobenzyl) malonate (31.8 g, 0.09 mol) and potassium hydroxide (10.3 g, 0.18 mol) in water (200 ml) was refluxed for 4.5 h. The mixture was concentrated in vacuo to remove the ethanol. To the resulting solution was added concentrated sulphuric acid (15.7 ml, 0.29 mol) and the mixture was refluxed for 18 h. The reaction mixture was chilled in an ice bath and the resulting solid was filtered, washed with water, and air dried to give 20.6 g (91%) of crude 3-(2-bromo-4-fluorophenyl) propionic acid. This material was used without further purification.

12
2-bromo-4-fluoro-1-iodobenzene [ No CAS ]
[ 174603-55-5 ]

References: [1]Patent: WO2013/144098,2013,A1 .

13
methyl 3-(2-bromo-4-fluorophenyl)propanoate [ No CAS ]
[ 174603-55-5 ]

Yield	Reaction Conditions	Operation in experiment
1.2 g		To a solution of methyl 3-(2-bromo-4-fluorophenyl)propanoate (1 .4 g) in tetrahydrofuran (10 mL) and methanol (10 mL) is added 4 M aqueous NaOH solution (10 mL) and the mixture is heated to 50C for 3 hours. The organic solvents are evaporated in vacuo the residue is diluted with water and washed with tert. -butyl- methyl-ether. The aqueous phase is neutralized by addition of 4 M hydrochloric acid (10 mL) and the mixture is stirred for 1 hour. The precipitate formed is filtered off, washed with water and dried to give the title compound. Yield: 1 .2 g; LC (method 3): tR = 0.71 min; Mass spectrum (ESI"): m/z = 245 [M-H]

References: [1]Patent: WO2013/144098,2013,A1 .Location in patent: Page/Page column 114.

14
[ 174603-55-5 ]
6-fluoro-1-oxo-indan-4-carbonitrile [ No CAS ]

References: [1]Patent: WO2015/36759,2015,A1 .

15
[ 174603-55-5 ]
ethyl 5-bromo-7-fluoro-3,4-dihydroisoquinoline-2(1H)-carboxylate [ No CAS ]

References: [1]Patent: US2016/115126,2016,A1 .

16
[ 174603-55-5 ]
5-bromo-7-fluoro-1,2,3,4-tetrahydroisoquinoline [ No CAS ]

References: [1]Patent: US2016/115126,2016,A1 .

17
[ 64-17-5 ]
[ 174603-55-5 ]
ethyl 2-bromo-4-fluorophenethylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With diphenyl phosphoryl azide; triethylamine; In tetrahydrofuran; at 80℃; for 18h;	A mixture of <strong>[174603-55-5]3-(2-bromo-4-fluorophenyl)propanoic acid</strong> (2.00 g, 8.10 mmol), EtOH (0.945 mL, 16.2 mmol), TEA (3.38 mL, 24.3 mmol) and diphenylphosphoryl azide (2.45 g, 8.90 mmol) in anhydrous THF (20 mL) was heated at 80 C. for 18 h. The mixture was concentrated and the residue was subjected to column chromatography on silica gel, eluting with EtOAc-hexanes (gradient from 0-100%) to provide ethyl 2-bromo-4-fluorophenethylcarbamate as a colorless gum (2.03 g, 82% yield). Mass spectrum m/z 290, 292 (M+H)+. 1H NMR (400 MHz, CDCl3) delta 7.31 (dd, J=8.3, 2.5 Hz, 1H), 7.24-7.16 (m, 1H), 6.99 (td, J=8.3, 2.6 Hz, 1H), 4.68 (br. s., 1H), 4.19-4.06 (m, 2H), 3.43 (q, J=6.6 Hz, 2H), 2.95 (t, J=6.9 Hz, 2H), 1.30-1.19 (m, 3H).

References: [1]Patent: US2016/115126,2016,A1 .Location in patent: Paragraph 0575-0576.

18
[ 2033-24-1 ]
[ 59142-68-6 ]
[ 174603-55-5 ]

References: [1]Organic Letters,2019,vol. 21,p. 9334 - 9338.
[2]Chemical Communications,2019,vol. 55,p. 13856 - 13859.

19
[ 174603-55-5 ]
(E)-3-(2-(3-(dibenzylamino)propyl)-5-fluorophenyl)acrylaldehyde [ No CAS ]