1238702-58-3|1-Phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole| Ambeed

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Quality Control of [ 1238702-58-3 ] Purity: 97% SDS Specification

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Product Details of [ 1238702-58-3 ]

CAS No. :	1238702-58-3
Formula :	C₁₅H₁₉BN₂O₂
M.W :	270.13
SMILES Code :	CC1(C)OB(OC1(C)C)C1=CC=NN1C1=CC=CC=C1
MDL No. :	MFCD23135814
InChI Key :	TZYVCRRPWKPCLH-UHFFFAOYSA-N
Pubchem ID :	58072367

Safety of [ 1238702-58-3 ]

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

Computational Chemistry of [ 1238702-58-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	20
Num. arom. heavy atoms	11
Fraction Csp3	0.4
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	80.04
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	36.28 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	2.91
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.17
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.	1.67
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	1.38
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.62

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.62
Solubility	0.0643 mg/ml ; 0.000238 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.	-3.33
Solubility	0.126 mg/ml ; 0.000465 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	-4.53
Solubility	0.00805 mg/ml ; 0.0000298 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	Yes
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.	-5.88 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<0.0
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)	2.98

Application In Synthesis of [ 1238702-58-3 ]

* 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 [ 1238702-58-3 ]

[ 1238702-58-3 ] Synthesis Path-Downstream 1~31

1
[ 76-09-5 ]
[ 1238702-56-1 ]
[ 1238702-58-3 ]

Yield	Reaction Conditions	Operation in experiment
64%	In toluene; at 10 - 40℃;	Reference Example 1321-Phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole To a mixture of (1-phenyl-1H-pyrazol-5-yl)boronic acid (8.57 g, 45.6 mmol) in toluene (86 mL) was added pinacol (5.39 g, 45.6 mmol) at room temperature. The mixture was heated to 40 C. for 2 days. The mixture was concentrated in vacuo and triturated with hexane to yield the title compound (7.93 g, 64% yield) as a pale yellow solid: 1H NMR (DMSO-d6, 300 MHz): delta ppm 1.23 (12H, s), 6.84 (1H, s), 7.34-7.59 (5H, m), 7.75 (1H, d, J=1.9 Hz)
19.8 g	In toluene; at 40℃; for 48h;	B) 1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1-Phenyl-1H-pyrazol-5-yl)boronic acid (25.0 g) was dissolved in toluene (700 mL), pinacol (18.0 g) was added thereto at room temperature, and the mixture was stirred at 40 C. for 2 days. The reaction mixture was diluted with dichloromethane, and the mixture was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting solid was collected by filtration, and washed with hexane to give the title compound (19.8 g). 1H NMR (400 MHz, CDCl3) delta 1.27 (12H, s), 6.89 (1H, d, J=1.6 Hz), 7.33-7.43 (3H, m), 7.52-7.55 (2H, m), 7.72 (1H, d, J=1.6 Hz).
19.8 g	In toluene; at 20 - 40℃; for 48h;	B) 1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1-Phenyl-1H-pyrazol-5-yl)boronic acid (25.0 g) was dissolved in toluene (700 mL), pinacol (18.0 g) was added at room temperature, and the mixture was stirred at 40 C. for 2 days. The reaction mixture was diluted with dichloromethane, washed successively with water and saturated brine, dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated. The resulting solid was collected by filtration, and washed with hexane to give the title compound (19.8 g). 1H NMR (400 MHz, CDCl3) delta 1.27 (12H, s), 6.89 (1H, d, J=1.6 Hz), 7.33-7.43 (3H, m), 7.52-7.55 (2H, m), 7.72 (1H, d, J=1.6 Hz).

19.8 g

In toluene; at 20 - 40℃; for 48h;

E) 1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1-Phenyl-1H-pyrazol-5-yl)boronic acid (25.0 g) was dissolved in toluene (700 mL), pinacol (18.0 g) was added at room temperature, and the mixture was stirred at 40 C. for 2 days. The reaction mixture was diluted with dichloromethane, washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting solid was collected by filtration and washed with hexane to give the title compound (19.8 g). 1H NMR (400 MHz, CDCl3) delta 1.27 (12H, s), 6.89 (1H, d, J=1.6 Hz), 7.33-7.43 (3H, m), 7.52-7.55 (2H, m), 7.72 (1H, d, J=1.6 Hz).

References: [1]Patent: US2010/197651,2010,A1 .Location in patent: Page/Page column 73-74.
[2]Patent: US2013/150344,2013,A1 .Location in patent: Paragraph 0586; 0587.
[3]Patent: US2013/137700,2013,A1 .Location in patent: Paragraph 0449; 0450.
[4]Patent: US2013/137675,2013,A1 .Location in patent: Paragraph 0673; 0674.

2
[ 1238702-58-3 ]
[ 1238702-53-8 ]
[ 1238696-33-7 ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium acetate;bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); In water; butan-1-ol; for 16h;Reflux; Inert atmosphere;	Example 885-Methoxy-3-(1-phenyl-1H-pyrazol-5-yl)-1-quinolin-8-ylpyridazin-4(1H)-one A mixture of 3-bromo-5-methoxy-1-quinolin-8-ylpyridazin-4(1H)-one (70 mg, 0.217 mmol), <strong>[1238702-58-3]1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole</strong> (88.1 mg, 0.326 mmol), KOAc (42.6 mg, 0.434 mmol) and PdCl2{P(t-Bu)2(Ph-p-NMe2)}2 (7.7 mg, 0.0109 mmol) in BuOH (1.1 mL) and water (0.1 mL) was heated to reflux for 16 h under Ar atmosphere. The mixture was diluted with water, extracted with AcOEt, washed with saturated NaHCO3 aqueous solution, dried over Na2SO4, filtered, concentrated in vacuo, purified by column chromatography on basic silica gel (hexane/AcOEt=50/50 to 0/100 and AcOEt/MeOH=100/0 to 70/30) and recrystallized with AcOEt/hexane to yield the title compound (69.9 mg, 81% yield) as a white solid: mp 189-192 C. 1H NMR (DMSO-d6, 300 MHz): delta ppm 3.76 (3H, s), 6.98 (1H, s), 7.31-7.49 (6H, m), 7.58-7.73 (2H, m), 7.78 (1H, d, J=1.9 Hz), 8.14 (1H, d, J=8.3 Hz), 8.54 (1H, d, J=7.9 Hz), 8.67 (1H, s), 8.99 (1H, d, J=4.1 Hz). Anal. Calcd for C23H17N5O2: C, 69.86; H, 4.33; N, 17.71. Found: C, 69.61; H, 4.37; N, 17.57.

References: [1]Patent: US2010/197651,2010,A1 .Location in patent: Page/Page column 128.

3
[ 1238702-58-3 ]
[ 1238703-27-9 ]
[ 1238696-55-3 ]

Yield	Reaction Conditions	Operation in experiment
66%	With potassium carbonate;bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); In water; toluene; for 20h;Reflux; Inert atmosphere;	Example 965-Methoxy-1-(2,2,3,3,7-pentafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one A mixture of 3-bromo-5-methoxy-1-(2,2,3,3,7-pentafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)pyridazin-4(1H)-one (200 mg, 0.466 mmol), <strong>[1238702-58-3]1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole</strong> (189 mg, 0.699 mmol), K2CO3 (129 mg, 0.932 mmol) and PdCl2{P(t-Bu)2(Ph-p-NMe2)}2 (16.5 mg, 0.0233 mmol) in toluene (2.3 mL) and water (0.23 mL) was heated to reflux for 20 h under Ar. The mixture was diluted with water, brine and saturated NaHCO3 aqueous solution, extracted with AcOEt, dried over Na2SO4, filtered, concentrated in vacuo, purified by column chromatography on basic silica gel (hexane/AcOEt=50/50 to 0/100) and recrystallized with AcOEt/hexane to yield the title compound (150 mg, 66% yield) as a white solid: mp 192-194 C. 1H NMR (DMSO-d6, 300 MHz): delta ppm 3.76 (3H, s), 7.00 (1H, d, J=1.9 Hz), 7.28-7.48 (6H, m), 7.79 (1H, d, J=1.9 Hz), 7.93 (1H, d, J=10.5 Hz), 8.51 (1H, d, J=1.9 Hz). Anal. Calcd for C22H13F5N4O4: C, 53.67; H, 2.66; N, 11.38. Found: C, 53.73; H, 2.72; N, 11.33.

References: [1]Patent: US2010/197651,2010,A1 .Location in patent: Page/Page column 130-131.

4
[ 1238702-58-3 ]
[ 1357192-30-3 ]
[ 1357192-31-4 ]

Yield	Reaction Conditions	Operation in experiment
78%	With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); potassium carbonate; In water; toluene; for 24h;Reflux; Inert atmosphere;	A mixture of 11 (13.6 g, 54.3 mmol), <strong>[1238702-58-3]1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole</strong> (22.0 g, 81.0mmol), K2CO3 (51.0 g, 109 mmol) and PdCl2[Pt-Bu2(Ph-p-NMe2)]2(1.92 g, 2.71 mmol) in toluene (330 mL) and water (33 mL) wasrefluxed for 24 h under N2 atmosphere. The mixture was dilutedwith water and saturated NaHCO3 aqueous solution. The mixturewas extracted with EtOAc, dried over Na2SO4, and concentratedunder reduced pressure. The residue was recrystallized fromEtOAc/hexane to give 12 (15.1 g, 78%) as a pale yellow solid. 1HNMR (DMSO-d6) d 3.81 (3H, s), 5.10 (2H, s), 6.95(1H, d, J = 1.6 Hz), 7.05-7.07 (2H, m), 7.24-7.38 (8H, m), 7.74 (1H,d, J = 1.6 Hz), 8.33 (1H, s).
	With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); potassium carbonate; In water; toluene; for 24h;Reflux;	A mixture of l-benzyl-3-chloro-5-methoxypyridazin-4 (1H) -one (13.6 g) , l-phenyl-5- (4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2- yl) -lif-pyrazole (22.0 g) , potassium carbonate (51.0 g) and PdCl2{Pt-Bu2 (Ph-p-NMe2) }2 (1.92 g) in toluene (330 mL) and water (33.0 mL) was stirred at reflux for 24 hr under nitrogen atmosphere. The reaction mixture was diluted with water and saturated sodium hydrogen carbonate aqueous solution, extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by recrystallization from ethyl acetate/hexane to give the title compound (15.1 g) as a pale yellow solid. ¾ NMR (400 MHz, DMSO-d6) delta 3.81 (3H, s) , 5.10 (2H, s) , 6.95 (1H, d, J = 1.6 Hz), 7.05-7.07 (2H, m) , 7.24-7.38 (8H, m) , 7.74 (1H, d, J = 1.6 Hz) , 8.33 (1H, s) .
15.1 g	With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); potassium carbonate; In water; toluene; for 24h;Reflux; Inert atmosphere;	E) 1-benzyl-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one 1-Benzyl-3-chloro-5-methoxypyridazin-4(1H)-one (13.6 g), <strong>[1238702-58-3]1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole</strong> (22.0 g), potassium carbonate (51.0 g) and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (1.92 g) were suspended in toluene (330 mL) and water (33.0 mL), and the suspension was heated under reflux under a nitrogen atmosphere for 24 hr. The reaction mixture was allowed to be cooled to room temperature, diluted with water and saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was recrystallized from ethyl acetate/hexane to give the title compound (15.1 g). 1H NMR (400 MHz, DMSO-d6) delta 3.81 (3H, s), 5.10 (2H, s), 6.95 (1H, d, J=1.6 Hz), 7.05-7.07 (2H, m), 7.24-7.38 (8H, m), 7.74 (1H, d, J=1.6 Hz), 8.33 (1H, s).

15.1 g	With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); potassium carbonate; In water; toluene; for 24h;Reflux; Inert atmosphere;	E) 1-benzyl-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one 1-Benzyl-3-chloro-5-methoxypyridazin-4(1H)-one (13.6 g), <strong>[1238702-58-3]1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole</strong> (22.0 g), potassium carbonate (51.0 g) and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (1.92 g) were suspended in toluene (330 mL) and water (33.0 mL), and the mixture was heated under reflux under a nitrogen atmosphere for 24 hr. The reaction mixture was cooled to room temperature, diluted with water and saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated, and the residue was recrystallized from ethyl acetate/hexane to give the title compound (15.1 g). 1H NMR (400 MHz, DMSO-d6) delta 3.81 (3H, s), 5.10 (2H, s), 6.95 (1H, d, J=1.6 Hz), 7.05-7.07 (2H, m), 7.24-7.38 (8H, m), 7.74 (1H, d, J=1.6 Hz), 8.33 (1H, s).
15.1 g	With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); potassium carbonate; In water; toluene; at 24℃;Reflux; Inert atmosphere;	C) 1-benzyl-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one 1-Benzyl-3-chloro-5-methoxypyridazin-4(1H)-one (13.6 g), <strong>[1238702-58-3]1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole</strong> (22.0 g), potassium carbonate (51.0 g) and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (1.92 g) were suspended in toluene (330 mL) and water (33.0 mL), and the mixture was heated under reflux for 24 hr under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, diluted with water and saturated aqueous sodium hydrogen carbonate solution, extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered, concentrated, and recrystallized from ethyl acetate/hexane to give the title compound (15.1 g). 1H NMR (400 MHz, DMSO-d6) delta 3.81 (3H, s), 5.10 (2H, s), 6.95 (1H, d, J=1.6 Hz), 7.05-7.07 (2H, m), 7.24-7.38 (8H, m), 7.74 (1H, d, J=1.6 Hz), 8.33 (1H, s).

References: [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 3447 - 3455.
[2]Patent: WO2013/27845,2013,A1 .Location in patent: Paragraph 0409.
[3]Patent: US2013/150344,2013,A1 .Location in patent: Paragraph 0592; 0593.
[4]Patent: US2013/137700,2013,A1 .Location in patent: Paragraph 0455; 0456.
[5]Patent: US2013/137675,2013,A1 .Location in patent: Paragraph 0741; 0742.

5
[ 1126-00-7 ]
[ 1238702-58-3 ]

References: [1]Patent: US2013/150344,2013,A1 .
[2]Patent: US2013/137700,2013,A1 .
[3]Patent: US2013/137675,2013,A1 .

6
[ 1238702-58-3 ]
[ 1357192-32-5 ]

References: [1]Patent: US2013/150344,2013,A1 .
[2]Patent: US2013/137700,2013,A1 .
[3]Patent: US2013/137675,2013,A1 .

7
[ 1238702-58-3 ]
[ 1357590-67-0 ]

References: [1]Patent: US2013/137675,2013,A1 .

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[ 1238702-58-3 ]
[ 1357590-79-4 ]

References: [1]Patent: US2013/137675,2013,A1 .

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[ 1238702-58-3 ]
[ 1357590-85-2 ]

References: [1]Patent: US2013/137675,2013,A1 .

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[ 1238702-58-3 ]
[ 1357591-77-5 ]

References: [1]Patent: US2013/137675,2013,A1 .

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[ 1238702-58-3 ]
[ 1357591-80-0 ]

References: [1]Patent: US2013/137675,2013,A1 .

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[ 1238702-58-3 ]
[ 1357592-87-0 ]

References: [1]Patent: US2013/137675,2013,A1 .

13
[ 1238702-58-3 ]
[ 1357358-24-7 ]

References: [1]Patent: US2013/137675,2013,A1 .

14
[ 1238702-58-3 ]
[ 1357589-28-6 ]
[ 1357589-17-3 ]

Yield	Reaction Conditions	Operation in experiment
0.0087 g	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 100℃; for 6h;Inert atmosphere;	E) 5-(1-phenyl-1H-pyrazol-5-yl)-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one 5-oxo-2-[3-(trifluoromethyl)phenyl]-2,5-dihydropyridazin-4-yl trifluoromethanesulfonate (0.100 g), <strong>[1238702-58-3]1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole</strong> (0.139 g), sodium carbonate (0.109 g) and tetrakis(triphenylphosphine)palladium(0) (0.0298 g) were suspended in a mixed solvent of toluene (2.06 mL), ethanol (0.52 mL) and water (0.52 mL), and the suspension was stirred at 100 C. for 6 hr under an argon atmosphere. The reaction mixture was cooled to room temperature, diluted with water, extracted with ethyl acetate, washed with aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated, purified by NH silica gel column chromatography (ethyl acetate/hexane) and recrystallized from ethyl acetate/hexane to give the title compound (0.0087 g). MS (ESI+): [M+H]+ 383.3.

References: [1]Patent: US2013/137675,2013,A1 .Location in patent: Paragraph 0725; 0726.

15
5-(2-fluorophenyl)pyridin-2(1H)-one [ No CAS ]
[ 1238702-58-3 ]
[ 1357589-31-1 ]

Yield	Reaction Conditions	Operation in experiment
0.0007 g	With pyridine; copper diacetate; for 54h;Reflux;	B) 5-(2-fluorophenyl)-1-(1-phenyl-1H-pyrazol-5-yl)pyridin-2(1H)-one 5-(2-Fluorophenyl)pyridin-2(1H)-one (0.0281 g), <strong>[1238702-58-3]1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole</strong> (0.0802 g) and copper(II) acetate (0.0539 g) were suspended in pyridine (1.48 mL), and the suspension was stirred at room temperature for 12 hr and further at 90 C. for 6 hr. To the reaction mixture were added <strong>[1238702-58-3]1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole</strong> (0.0802 g) and copper(II) acetate (0.0539 g) at room temperature, and the mixture was heated under reflux for 1.5 days. The reaction mixture was cooled to room temperature, purified by NH silica gel column chromatography (ethyl acetate/hexane) and recrystallized from ethyl acetate/hexane to give the title compound (0.0007 g). MS (ESI+): [M+H]+ 332.2.

References: [1]Patent: US2013/137675,2013,A1 .Location in patent: Paragraph 20.

16
[ 1238702-58-3 ]
[ 1357358-22-5 ]