775351-57-0|2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile| Ambeed

Structure of 775351-57-0

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Quality Control of [ 775351-57-0 ] Purity: 97% SDS Specification

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Product Details of [ 775351-57-0 ]

CAS No. :	775351-57-0
Formula :	C₁₃H₁₅BFNO₂
M.W :	247.07
SMILES Code :	CC1(C)OB(OC1(C)C)C1=CC(C#N)=C(F)C=C1
MDL No. :	MFCD06795681
InChI Key :	RYJOVQGRIOURGT-UHFFFAOYSA-N
Pubchem ID :	11402361

Safety of [ 775351-57-0 ]

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

Computational Chemistry of [ 775351-57-0 ] 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)	2.97

Application In Synthesis of [ 775351-57-0 ]

* 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 [ 775351-57-0 ]

[ 775351-57-0 ] Synthesis Path-Downstream 1~41

1
[ 775351-57-0 ]
5-[2-fluoro-5-(boronic acid)-phenyl]-1H-tetrazole [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 3265 - 3268.

2
[ 179897-89-3 ]
[ 73183-34-3 ]
[ 775351-57-0 ]

Yield	Reaction Conditions	Operation in experiment
81%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; at 100.0℃;Sealed tube;	2-Fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile A mixture of 5-Bromo-2-fluoro-benzonitrile (1000.00 mg; 5.00 mmol; 1.00 eq.), 4,4,5,5,4',4',5',5'-Octamethyl-[2,2']bi[[1,3,2]dioxaborolanyl] (1396.61 mg; 5.50 mmol; 1.10 eq.), potassium acetate (1472.07 mg; 15.00 mmol; 3.00 eq.) in dioxane (10 mL) and DMf (1 mL) was degassed, then [1,1']-bis(diphenyl phosphino) ferrocene]dichloropalladium(II), complex with dichloromethane(1:) (366.85 mg; 0.50 mmol; 0.10 eq.) was added and the sealed vial was heated at 100 C. for overnight. The reaction mixture was cooled and filtered through a pad of Celite. The solvent was removed and the crude product was purified through flash chromatography on silica gel (EtOAc:hexanes from 0% to 5%) to obtain 2-Fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile (1.0 g, 81%)
72%	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 100.0℃;Inert atmosphere;	6(pinacolato)diboron (1.9 g, 7.48 mmol), and KOAc (1.47 g, 14.98 mmol) in 1,4- dioxane (10.0 mL) that was degassed with argon for 10 min was added PdCl2(dppf) (10 mg, 0.014 mmol). The reaction mixture was heated to 100 0C overnight. The reaction mixture was filtered through Celite 521 and rinsed through with EtOAc (10 mL). The filtrate was concentrated in vacuo and treated with CH2Cl2 (10 mL) and water (10 mL). The layers were separated, and the aqueous layer was extracted with CH2Cl2 (5 mL). The combined organic layers were washed with brine (5 mL), dried over Na2SO4, filtered, and concentrated in vacuo onto Isolute. Purification via flash column chromatography (0- 20% EtOAc/hexanes) afforded the title compound (1.03 g, 72%). LC-MS m/z 248 (M+H)+, 1.15 min (ret time).

References: [1]Patent: US2016/376283,2016,A1 .Location in patent: Paragraph 0504; 0505; 0506.
[2]Patent: WO2011/25799,2011,A1 .Location in patent: Page/Page column 50.
[3]Chemistry - An Asian Journal,2019,vol. 14,p. 2251 - 2258.
[4]Organic Letters,2004,vol. 6,p. 3265 - 3268.

3
[ 775351-57-0 ]
[ 944804-72-2 ]
tert-butyl (S)-1-(5-(3-cyano-4-fluorophenyl)thiazol-2-ylamino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 120.0℃; for 0.341667h;Microwave irradiation;	To a solution of (S)-tert-butyl 1-(N-(5-bromothiazol-2-yl)-tert-butoxylcarbonylamino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate (0.20 g, 0.34 mmol) in 3 mL of dioxane in a microwave safe tube, was added <strong>[775351-57-0]2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile</strong> (0.13 g, 0.52 mmol), sodium carbonate, 2 M in water (0.69 mL, 1.4 mmol), and tetrakis(triphenylphosphine) palladium (0.020 g, 0.017 mmol). The mixture was purged with nitrogen for 30 seconds and the tube was sealed. The tube was then heated to 120 C. in a Personal Chemistry microwave unit for 20 minutes. The mixture was diluted with 5 mL of water and extracted twice with 8 mL of EtOAc. The combined organic extracts were washed with 7 mL of brine and dried over MgSO4. Filtration and concentration under reduced pressure afforded tert-butyl (S)-1-(5-(3-cyano-4-fluorophenyl)thiazol-2-ylamino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate, mixed with the other two products. The crude mixture was carried on to the next reaction without any further purification.

References: [1]Patent: US2007/173506,2007,A1 .Location in patent: Page/Page column 49.

5
[ 775351-57-0 ]
[ 944804-72-2 ]
[ 1221541-31-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1559 - 1564.

6
[ 775351-57-0 ]
[ 3034-53-5 ]
2-fluoro-5-(thiazol-2-yl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.9%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100.0℃; for 2.5h;Microwave irradiation;	To a mixture of 2-fluoro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)- benzonitrile (100 mg, 0.405 mmol), 2-bromothiazole (0.11 mL, 1.221 mmol), and K2CO3 (168 mg, 1.214 mmol) in 1,4-dioxane (1.5 mL) and water (0.5 mL) was added Pd(Ph3P)4 (5 mg, 0.004 mmol). The vial was capped and the reaction mixture was heated in a Biotage Initiator microwave reactor to 100 0C for 30 min followed by an additional 2 h at 100 0C. Water (4 mL) and EtOAc (5 mL) were added to the reaction mixture. The layers were separated, and the aqueous layer was extracted with EtOAc (2 x 3 mL). The combined organic layers were washed with brine (3 x 1 mL) and concentrated under a stream of nitrogen at 50 0C onto Isolute. Purification via flash column chromatography (0-20% EtOAc/hexanes) afforded the title compound (2.4 mg, 2.9%). LC-MS m/z 205 (M+H)+, 0.87 min (ret time).

References: [1]Patent: WO2011/25799,2011,A1 .Location in patent: Page/Page column 50-51.

7
[ 775351-57-0 ]
[ 4595-60-2 ]
[ 1269406-96-3 ]