624741-47-5|3-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile| Ambeed

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Quality Control of [ 624741-47-5 ] Purity: 96% SDS Specification

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Product Details of [ 624741-47-5 ]

CAS No. :	624741-47-5
Formula :	C₁₃H₁₅BFNO₂
M.W :	247.07
SMILES Code :	N#CC1=CC=CC(F)=C1B2OC(C)(C)C(C)(C)O2
MDL No. :	MFCD09260444
InChI Key :	HIMZNJDDVIROEC-UHFFFAOYSA-N
Pubchem ID :	22240104

Safety of [ 624741-47-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H317-H319
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 624741-47-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	18
Num. arom. heavy atoms	6
Fraction Csp3	0.46
Num. rotatable bonds	1
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	67.59
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	42.25 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.0
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	2.73
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.42
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.	1.45
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	2.26
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.77

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.27
Solubility	0.132 mg/ml ; 0.000534 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.	-3.27
Solubility	0.132 mg/ml ; 0.000535 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	-4.37
Solubility	0.0106 mg/ml ; 0.0000429 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	Yes
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	No
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	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.87 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	1.0 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)	3.04

Application In Synthesis of [ 624741-47-5 ]

* 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 [ 624741-47-5 ]

[ 624741-47-5 ] Synthesis Path-Downstream 1~19

2
[ 624741-47-5 ]
[ 628323-26-2 ]
3-fluoro-2-{6-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-a]pyridin-3-yl]pyridin-2-yl}benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 150.0℃; for 0.25h;	[2- (8-FLUOROIMIDAZO [1,] 2-a] [PYRIDIN-7-YL)] propan-2-ol (194 mg, 1.0 mmol) was coupled with 2,6-dibromopyridine (403 mg, 1.7 mmol) using [CS2CO3] (652 mg, 2.0 mmol), as described in Example 4, affording [2- [3- (6-] [BROMOPYRIDIN-2-YL)-8-FLUOROIMIDAZO] [1, 2-a] pyridin-7-yl] propan-2-ol as a white amorphous solid (210 mg, 60%): [M/Z] (ES+) 350,352 [(100%,] [MH] +). 2- [[3-(6-BROMOPYRIDIN-2-YL)-8-FLUOROIMIDAZO [1,] 2-a] pyridin-7- yl] propan-2-ol (50 mg, 0.143 [MMOL),] [3-FLUORO-2- (4,] 4,5, 5-tetramethyl- [1, 3,2] dioxaborolan-2-yl) benzonitrile (53 mg, 0.214 mmol) and tetrakis (triphenylphosphine) palladium [(0)] (8.3 mg, 0.0714 mmol) were suspended in 1,2-dimethoxyethane (3 ml) and 2N sodium carbonate solution (0.5 ml) and heated to [150C] for 900 s in a Smith Personal [SYNTHESISERTM] using microwave irradiation. The mixture was allowed to cool to ambient temperature, diluted with water (75 ml) and extracted into ethyl acetate (2 [X 75] ml). The combined organic phase was washed with water (50 ml) and brine (50 ml), dried over anhydrous sodium sulfate, filtered and evaporated to give an orange oil. The oil was purified by preparative-plate chromatography on silica eluting with dichloromethane: methanol : 0.880 ammonia (97: 3: 0.3). Collecting the appropriate fraction followed by trituration with diethyl ether (5 ml) and recrystallisation from ethyl [ACETATE/ISOHEXANE] gave the title imidazopyridine as a white amorphous solid (20 mg, 36%): [8S] (360 MHz, CDCl3) 1.73 (6H, s), 2.07 [(1H,] d, [J 1. 1),] 7.25 [(1H,] t, [J 7.] 0), 7.46-7. 59 (3H, m), 7.69 [(1H,] s), 7.84-7. 94 (2H, m), 8.20 [(1H,] s), 9.72 [(1H,] d, [J 7.] 4); [M/Z] (ES+) 391 (100%, [[MH] +).]

References: [1]Patent: WO2003/99817,2003,A1 .Location in patent: Page 42.

3
[ 73183-34-3 ]
[ 425379-16-4 ]
[ 624741-47-5 ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; dimethyl sulfoxide; at 90.0℃; for 18.0h;	A mixture of 2-bromo-3-fluorobenzonitrile (1.20 g, 6.00 mmol), dried potassium acetate (1.18 g, 12.0 mmol) and bis (pinacolato) diboron (1.75 g, 6.89 mmol) in 1, 4-dioxan (14.7 ml) and dimethylsulfoxide (0.3 ml) was degassed by bubbling nitrogen through the mixture for 50 min. Dichloro [l, 1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloromethane adduct (0.1481 g, 0.181 mmol) was added and the mixture was degassed for a further 10 min, then heated at 90C under nitrogen for 18 h. After allowing to cool, the mixture was filtered through glass fibre paper, and the solid was washed with a little dichloromethane. The combined filtrates were evaporated in vacuo and the residue was partitioned between 2 M aqueous NaOH (21 ml) and diethyl ether (20 ml). The aqueous layer was then acidified to pH 5 with concentrated hydrochloric acid (3 ml), causing a solid to precipitate. After leaving in a fridge for 3 days, the solid was collected by filtration, washed with water and dried under vacuum to leave 0.9191 g (62%) of the title compound as a white solid: 1H NMR (360 MHz, DMSO-d6) 8 1.34 (12H, s), 7.55-7. 59 (1H, m), 7.69-7. 75 (2H, m).

References: [1]Patent: WO2003/93272,2003,A1 .Location in patent: Page/Page column 37.
[2]Organic Letters,2011,vol. 13,p. 1366 - 1369.

4
[ 624741-47-5 ]
[ 103977-79-3 ]
[ 624741-53-3 ]

Yield	Reaction Conditions	Operation in experiment
67%	With potassium fluoride;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In tetrahydrofuran; 1,4-dioxane; at 50.0℃; for 18.0h;	c) 3'-Amino-6, 2'*6'-trilluorobiphensl-2-carbonitrile; A mixture of 3-bromo-2, 4-difluorophenylamine (0.6451 g, 3. 10 mmol) and 3-fluoro-2- (4, 4,5, 5-tetramethyl- [1, 3,2] dioxaborolan-2- yl) benzonitrile (0.915 g, 3.70 mmol) and potassium fluoride (0.5953 g, 10.2 mmol) in tetrahydrofuran (8 ml) was degassed with nitrogen for 15 min before adding tris (dibenzylideneacetone) dipalladium (0) (56.9 mg, 0.0621 mmol) and tri-tert-butylphosphine (1.24 ml of a 0.1 M solution in 1,4- dioxane, 0.124 mmol). The mixture was degassed for a further 5 min, then heated at 50C for 18 h under nitrogen. After cooling to ambient temperature, the mixture was partitioned between water (50 ml) and ethyl acetate (40 ml). The organic layer was washed with saturated aqueous NaCl (20 ml), dried (Na2SO4) and evaporated in vacuo. The residue was purified by chromatography (silica gel, 30% EtOAc/isohexane) to afford 0. 5180 g (67%) of the title compound as a yellow solid: zu NMR (360 MHz, CDC13) 8 3.70 (2H, br s), 6.84-6. 92 (2H, m), 7.44 (1H, t, J 8. 4), 7.53 (1H, td, J 8. 2,5. 1), 7.61 (1E, d, J 7. 3).

References: [1]Patent: WO2003/93272,2003,A1 .Location in patent: Page/Page column 38-39.

5
[ 624741-47-5 ]
[ 765916-78-7 ]
[ 765916-85-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine)palladium (0); In 1,4-dioxane; dichloromethane;	EXAMPLE 12 6,2'-Difluoro-5'-[3-(2,4-difluorophenyl)-[1,2,4]triazin-5-yl]biphenyl-2-carbonitrile To a degassed mixture of 5-(3-bromo-4-fluorophenyl)-3-(2,4-difluorophenyl)-[1,2,4]triazine (0.2 g, 0.55 mmol) and <strong>[624741-47-5]3-fluoro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzonitrile</strong> (0.270 g, 1.1 mmol) in 1,4-dioxane (6 ml) and sodium carbonate (2 ml, 2N solution) was added tetrakis(triphenylphosphine)palladium(0), and the mixture heated at 80 C. for 24 h. The mixture was cooled to ambient temperature and partitioned between water (30 ml) and dichloromethane (40 ml). The aqueous layer was extracted with dichloromethane (2*40 ml) and the combined organics dried over Mg2SO4, filtered and the solvent removed at reduced pressure. The crude product was chromatographed on silica gel, eluent 5% ethyl acetate in dichloromethane, to give the product as a pale yellow solid (0.014 g): deltaH (400 MHz, CDCl3) 6.99-7.10 (2H, m), 7.49 (4H, m), 8.30-8.44 (3H, m), 9.69 (1H, dd, J 0.8, 2.0 Hz); m/z (ES+) 407.

References: [1]Patent: US2004/192692,2004,A1 .

6
[ 624741-47-5 ]
[ 4595-60-2 ]
[ 1293285-05-8 ]

Yield	Reaction Conditions	Operation in experiment
64%	With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); sodium carbonate; In tetrahydrofuran; water; at 80.0℃; for 5.16667h;Inert atmosphere;	Synthesis of 3-fluoro-2-(pyrimidin-2-yl)benzonitrile (Intermediate in the synthesis of intermediate A-2) To a solution of <strong>[624741-47-5]3-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile</strong> (4.98 g, 19.1 mmol) and 2-bromopyridine (3.85 g, 23 mmol) in THF (96 mL) was added Na2CO3 (6 g, 57.4 mmol) followed by water (43 mL). The reaction mixture was degassed with N2 for 10 minutes. PdCl2(dtbpf) (374 mg, 0.57 mmol) was added and the reaction mixture was stirred at 80 C. for 5 h. The solution was cooled to room temperature and a mixture of EtOAc and water was added. The aqueous was extracted twice with EtOAc and the combined organic layers were dried over MgSO4, filtered and evaporated. The title compound was precipitated by dissolving the residue in a minimum amount of EtOAc and then adding hexanes. The solid was filtered, washed with hexanes and dried to afford the title compound (2.46 g, 64%). MS (ESI) mass calcd. for C11H6FN3, 199.1; m/z found 200.1 [M+H]+. 1H NMR (400 MHz, Chloroform-d) delta 9.02-8.91 (m, 2H), 7.65 (dt, J=7.7, 1.0 Hz, 1H), 7.60-7.52 (m, 1H), 7.51-7.43 (m, 1H), 7.41 (t, J=4.9 Hz, 1H).
64%	With dichloro[1,1?-bis[bis(1,1-dimethylethyl)phosphino]ferrocene-P,P?]palladium; sodium carbonate; In tetrahydrofuran; water; at 80.0℃; for 5.0h;Inert atmosphere;	10286] To a solution of 3-fluoro-2-(4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)benzonitrile (4.98 g, 19.1 mmol) and2-bromopyrimidine (3.85 g, 23 mmol) in THF (96 mE) was added Na2CO3 (6 g, 57.4 mmol) followed by water (43 mE). The reaction mixture was degassed with N2 for 10 minutes. PdC12(dtbpf) (374 g, 0.57 mmol) was added and the reaction mixture was stirred at 800 C. for 5 h. The solution was cooled to room temperature and a mixture of EtOAc and water was added. The aqueous was extracted twice with EtOAc and the combined organic layers were dried over Mg504, filtered and evaporated. The title compound was precipitated by dissolving the residue in a minimum amount of EtOAc and then adding hexanes. The solid was filtered, washed with hexanes and dried to afford the title compound (2.46 g, 64%). MS (ESI) mass calcd. for C,,H6FN3, 199.1; mlz found 200.1 [M+H]. ?H NMR (400 MHz, Chloroform-d) oe 9.02-8.91 (m, 2H), 7.65 (dt, J7.7, 1.0 Hz, 1H), 7.60-7.52 (m, 1H), 7.5 1-7.43 (m, 1H), 7.41 (t, J4.9 Hz, 1H).
64%	With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); sodium carbonate; In tetrahydrofuran; water; at 80.0℃; for 5.0h;	Synthesis of 3-fluoro-2-(pyrimidin-2-yl)benzonitrile (Intermediate in the synthesis of intermediate A-2) To a solution of <strong>[624741-47-5]3-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile</strong> (4.98 g, 19.1 mmol) and 2-bromopyrimidine (3.85 g, 23 mmol) in THF (96 mL) was added Na2CO3 (6 g, 57.4 mmol) followed by water (43 mL). The reaction mixture was degassed with N2 for 10 minutes. PdCl2(dtbpf) (374 mg, 0.57 mmol) was added and the reaction mixture was stirred at 80 C. for 5 h. The solution was cooled to room temperature and a mixture of EtOAc and water was added. The aqueous was extracted twice with EtOAc and the combined organic layers were dried over MgSO4, filtered and evaporated. The title compound was precipitated by dissolving the residue in a minimum amount of EtOAc and then adding hexanes. The solid was filtered, washed with hexanes and dried to afford the title compound (2.46 g, 64%). MS (ESI) mass calcd. for C11H6FN3, 199.1. m/z found 200.1 [M+H]+. 1H NMR (400 MHz, Chloroform-d) delta 9.02-8.91 (m, 2H), 7.65 (dt, J=7.7, 1.0 Hz, 1H), 7.60-7.52 (m, 1H), 7.51-7.43 (m, 1H), 7.41 (t, J=4.9 Hz, 1H).

References: [1]Patent: US2014/275118,2014,A1 .Location in patent: Paragraph 0142; 0143.
[2]Patent: US2016/46640,2016,A1 .Location in patent: Paragraph 0285; 0286.
[3]Patent: US2016/75696,2016,A1 .Location in patent: Paragraph 0216; 0217.

7
[ 624741-47-5 ]
(3-fluoro-2-(pyrimidin-2-yl)phenyl)((1S,2R,4R)-2-((5-(trifluoromethyl)pyridin-2-yl)amino)-7-azabicyclo[2.2.1]heptan-7-yl)methanone [ No CAS ]