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Chemical Structure| 1092485-88-5 Chemical Structure| 1092485-88-5

Structure of 1092485-88-5

Chemical Structure| 1092485-88-5

2-(3,5-Dichloro-4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

CAS No.: 1092485-88-5

4.5 *For Research Use Only !

Cat. No.: A230852 Purity: 97%

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Product Details of [ 1092485-88-5 ]

CAS No. :1092485-88-5
Formula : C12H14BCl2FO2
M.W : 290.95
SMILES Code : CC1(C)OB(OC1(C)C)C1=CC(Cl)=C(F)C(Cl)=C1
MDL No. :MFCD15143599
InChI Key :AISYFYGVRMYFTA-UHFFFAOYSA-N
Pubchem ID :53217183

Safety of [ 1092485-88-5 ]

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

Computational Chemistry of [ 1092485-88-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 18
Num. arom. heavy atoms 6
Fraction Csp3 0.5
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 72.9
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

18.46 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

4.26
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

3.85
Log Po/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.

3.21
Log Po/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

3.53
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.97

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-4.51
Solubility 0.00902 mg/ml ; 0.000031 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-4.36
Solubility 0.0127 mg/ml ; 0.0000437 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately 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

-5.5
Solubility 0.000918 mg/ml ; 0.00000316 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

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

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

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.05 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.

0.55

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

2.0 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)

2.96

Application In Synthesis of [ 1092485-88-5 ]

* 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 [ 1092485-88-5 ]

[ 1092485-88-5 ] Synthesis Path-Downstream   1~18

  • 1
  • [ 2268-05-5 ]
  • [ 73183-34-3 ]
  • [ 1092485-88-5 ]
YieldReaction ConditionsOperation in experiment
72.5% With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 2-(((2,6-diisopropylphenyl)imino)methyl)pyridine; In n-heptane; for 18h;Reflux; Step 1: Preparation of 2-(3,5-dichloro-4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 4,4,4',4',5,5,5',5'-Octamethyl[2,2'-bi-1,3,2-dioxaborolane] (2.0 g, 7.88 mmol), 2,6-bis(1-methylethyl)-N-(2-pyridinylmethylene)benzenamine (0.080 g, 0.30 mmol), and bis(1,5-cyclooctadiene)diiridium dichloride (0.132 g, 0.20 mmol) were added to a solution of <strong>[2268-05-5]1,3-dichloro-2-fluorobenzene</strong> (2.0 g, 12.12 mmol) in heptane (40 mL). The reaction mixture turned from yellow to forest green to brick red within the first minute. The reaction mixture was refluxed for 18 h. The mixture was then partitioned between EA and water, and the aqueous extract was washed twice with EA. The organic extracts were combined, dried over Na2SO4, and concentrated under reduced pressure. The solid residue was purified by chromatography on silica gel eluted with PE-EA (10:1) to give 2-(3,5-dichloro-4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.56 g, yield 72.5%) as a white solid. 1H NMR (500 MHz, CDCl3): delta 7.646 (d, J=6.5 Hz, 2H), 1.266 (s, 12H) ppm.
With 2-(((2,6-diisopropylphenyl)imino)methyl)pyridine;bis(1,5-cyclooctadiene)diiridium(I) dichloride; In n-heptane; for 18h;Heating / reflux; 4,4,4>,4>,5,5,5',5'-Octamethyl[2,2'-bi-1,3,2-dioxaborolane] (10.0 g, 39.4 mmol), 2,6- bis(l-methylethyl)-N-(2-pyridinylmethylene)benzenamine (0.40 g, 1.5 mmol), and i-mu- chlorobis[(1,2,5,6- eta)-1,5-cyclooctadiene]diiridium (0.50 g, 1.0 mmol) were added to a solution of <strong>[2268-05-5]1,3-dichloro-2-fluorobenzene</strong> (10.0 g, 60.6 mmol) in heptane (200 mL). The reaction mixture turned from yellow to forest green to brick red within the first minute. The reaction mixture was heated to reflux for 18 h. The mixture was then partitioned between ethyl acetate and water, and the aqueous extract was washed twice with ethyl acetate. The organic extracts were combined, dried over MgSOphi and concentrated under reduced pressure. The solid residue was purified by chromatography on silica gel by elution with ethyl acetate/hexane to afford the title compound as a solid (11.0 g). 1H NMR (CDCl3) delta 7.72 (d, 2H), 1.33 (s, 12H).
With 2-(((2,6-diisopropylphenyl)imino)methyl)pyridine;bis(1,5-cyclooctadiene)diiridium(I) dichloride; In n-heptane; for 18h;Heating / reflux; Step B: Preparation of 2-(3,5-dichloro-4-fluorophenyl)-4,4,5,5-tetramethyl-l,3,2- dioxaborolane; M^'^'^^^'^'-Octamethyip^'-bi-l^^-dioxaborolane] (10.0 g, 39.4 mmol), 2,6- bis(l-methylethyl)-iV-(2-pyridinylmethylene)benzenamine (0.40 g, 1.5 mmol), and di-mu- chlorobis[(l,2,5,6-?7)-l,5-cyclooctadiene]diiridium (0.50 g, 1.0 mmol) were added to a solution of l,3-dichloro-2-fluorobenzene (10.0 g, 60.6 mmol) in heptane (200 mL). The reaction mixture turned from yellow to forest green to brick red within the first minute. The reaction mixture was heated to reflux for 18 h. The mixture was then partitioned between ethyl acetate and water, and the aqueous extract was washed twice with ethyl acetate. The <n="13"/>organic extracts were combined, dried over MgSC«4, and concentrated under reduced pressure. The solid residue was purified by chromatography on silica gel by elution with ethyl acetate/hexane to afford the title compound as a solid (11.0 g). 1H NMR (CDCl3) delta 7.72 (d, 2H), 1.33 (s, 12H).
  • 2
  • [ 1514-82-5 ]
  • [ 1092485-88-5 ]
  • [ 928783-84-0 ]
YieldReaction ConditionsOperation in experiment
56% With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate; In tetrahydrofuran; at 70.0℃; for 4.0h;Sealed tube; Step 2: Preparation of 1,3-dichloro-2-fluoro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene A mixture of <strong>[1092485-88-5]2-(3,5-dichloro-4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane</strong> (2.56 g, 8.83 mmol), 2-bromo-3,3,3-trifluoroprop-1-ene (1.85 g, 10.6 mmol), Cs2CO3 (11.5 mL, 2M, 17.7 mmol) and Pd(PPh3)2Cl2 (200 mg) in THF (30 mL) was heated at 70 C. in a sealed tube for 4 h. The mixture was cooled to rt and partitioned between ether and H2O. The aqueous layer was extracted with EA and the combined organic layers were dried over Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica gel eluted with hexanes to give 1,3-dichloro-2-fluoro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (1.3 g; yield 56%) as colorless oil. 1H NMR (500 MHz, CDCl3): δ 7.412 (d, J=6.5 Hz, 2H), 6.057 (s, 1H), 5.806 (s, 1H) ppm.
47% With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; water; at 80.0℃; for 18.0h;Reflux; Preparation 2. 1,3-dichloro-2-fluoro-5-(1,1,1-trifluoroprop-2-en-2-yl)benzeneTo a stirred solution of 2-bromo-3,3,3-trifluoropropene (2.65 g, 15.1 mmol) and <strong>[1092485-88-5]2-(3,5-dichloro-4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane</strong> (2A.1) (4.4 g, 15.1 mmol) in 1,4-dioxane (60 mL) was added Na2CO3 (4.02 g, 38 mmol) and water (20 mL). Next, bis(triphenylphosphine) palladium II chloride (220 mg, 0.3 mmol) was added and the reaction mixture was heated to 80 C. for 18 hours. The reaction mixture was cooled, filtered, and concentrated under reduced pressure to remove dioxane. The residue was diluted with water (100 mL) and extracted with EtOAc (2×125 mL), dried (Na2SO4), and concentrated under vacuum. Crude material was purified on silica gel with 100% heptane to afford the intermediate as a clear oil (1.8 g, 47%). 1H NMR (CDCl3): δ 7.43 (2H), 6.07 (1H), 5.82 (1H).
With potassium hydroxide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; 1,2-dimethoxyethane; water; at 75.0℃; for 6.0h; 2-(3,5-Dichloro-4-fiuorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (11.0 g, 37.8 mmol) and 2-bromo-3,3,3-trifluoropropene (8.0 g, 46 mmol) were added to a mixture of tetrahydrofuran (30 niL), ethylene glycol dimethyl ether (30 mL), and 4 M potassium hydroxide aqueous solution (30 mL) in a 200 mL Fisher-Porter sealed tube, followed by the addition of tetrakis(triphenylphosphine)palladium(0) (264 mg, 0.229 mmol). The reaction mixture was heated at 75 C for 6 h. The reaction mixture was then partitioned between ether and water, and the aqueous layer was separated and washed twice with diethyl ether. The combined organic extracts were dried over MgSθ4 and concentrated under reduced pressure. The residual oily solid was purified by chromatography on silica gel by elution with ethyl acetate/hexane to afford the title compound as an oil (8.33 g). 1H NMR (CDCI3) δ 7.40 (d, 2H), 6.04 (s, 1H), 5.79 (s, 1H).
With potassium hydroxide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; 1,2-dimethoxyethane; water; at 75.0℃; for 6.0h; Step C : Preparation of 1 ,3 -dichloro-2-fluoro-5 - [ 1 -(trifluoromethyl)ethenyl]benzene; 2-(3,5-Dichloro-4-fluorophenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (11.0 g, 37.8 mmol) and 2-bromo-3,3,3-trifluoropropene (8.0 g, 45.7 mmol) were added to a mixture of tetrahydrofuran (30 mL), ethylene glycol dimethyl ether (30 mL), and 4 M potassium hydroxide aqueous solution (30 mL) in a 200 mL Fisher-Porter sealed tube, followed by the addition of tetrakis(triphenylphosphine)palladium(0) (264 mg, 0.229 mmol). The reaction mixture was heated to 75 0C for 6 h. The reaction mixture was then partitioned between ether and water, and the aqueous layer was separated and washed twice with ether. The combined organic extracts were dried over MgSC^ and concentrated under reduced pressure. The residual oily solid was purified by chromatography on silica gel by elution with ethyl acetate/hexane to afford the title compound as an oil (8.33 g). 1H NMR (CDCl3) δ 7.40 (d, 2H), 6.04 (s, IH), 5.79 (s, IH).

  • 3
  • [ 1092485-88-5 ]
  • [ 1338473-66-7 ]
  • 4
  • [ 1092485-88-5 ]
  • [ 1338473-81-6 ]
  • 5
  • [ 1092485-88-5 ]
  • [ 1338473-82-7 ]
  • 6
  • [ 1092485-88-5 ]
  • [ 1437779-30-0 ]
  • 9
  • [ 1092485-88-5 ]
  • [ 1437779-50-4 ]
  • [ 1437779-51-5 ]
  • 10
  • [ 17318-08-0 ]
  • [ 73183-34-3 ]
  • [ 1092485-88-5 ]
YieldReaction ConditionsOperation in experiment
78% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In toluene; at 110.0℃;Inert atmosphere; 5-bromo-1 ,3-dichloro-2-fluorobenzene (1 .00 equivalents), bis(pinacolato)diboron (1 .30 equivalents), Pd(dppf)Cl2 (0.05 equivalents) and potassium acetate (2.50 equivalents) are stirred under nitrogen atmosphere in toluene at 1 10 C until completion of the reaction (monitoring with GC/MS, usually finished within 4-16 h). Active carbon and Celite (kieselguhr) are added to the reaction mixture and stirred at 100 C for 10 minutes. Subsequently, the mixture is hot filtered and concentrated under reduced pressure. The obtained crude product is purified via column chromatography using a cyclohexane/ dichloromethane mixture (1 :1 ), giving E1 as solid (78 %).
78% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In toluene; at 110.0℃;Inert atmosphere; 5-bromo-1 ,3-dichloro-2-fluorobenzene (1 .00 equivalents), bis(pinacolato)diboron (1 .30 equivalents), Pd(dppf)Cl2 (0.05 equivalents) and potassium acetate (2.50 equivalents) are stirred under nitrogen atmosphere in toluene at 1 10 C until completion of the reaction (monitoring with GC/MS, usually finished within 4-16 h). Active carbon and Celite (also known as diatomaceous earth or kieselgur) are added to the reaction mixture and stirred at 100 C for 10 minutes. Subsequently, the mixture is hot filtered and concentrated under reduced pressure. The obtained crude product is purified via column chromatography using a cyclohexane/ dichloromethane mixture (1 :1 ), giving E1 as solid (78 %). AAV1 (78% yield), wherein 5-bromo-1 ,3-dichloro-2-fluorobenzene (CAS 17318-08-0) and bis(pinacolato)diboran (CAS 73183-34-3) were used as reactants
  • 11
  • [ 1092485-88-5 ]
  • C34H37B2FN2O4 [ No CAS ]
  • 12
  • [ 1092485-88-5 ]
  • C58H37FN4 [ No CAS ]
  • 13
  • [ 1092485-88-5 ]
  • C76H47N5O [ No CAS ]
  • 14
  • [ 1092485-88-5 ]
  • [ 29509-91-9 ]
  • C22H13Cl2FN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; water; at 110.0℃;Inert atmosphere; General procedure: E1 (1.00 equivalents), E2 (1 .15 equivalents), Pd(dppf)Cl2 (0.05 equivalents) and potassium acetate (2.50 equivalents) are stirred under nitrogen atmosphere in a mixture of dioxane and water (10:1 ) at 1 10 C until completion of the reaction (monitoring with GC/MS, usually finished within 4-24 h). Active carbon and Celite are added to the reaction mixture and stirred at 100 C for 10 minutes. Subsequently, the mixture is hot filtered and concentrated under reduced pressure. The residue is dissolved in dichloromethane and washed with water and brine. The organic phase is dried with MgS04, filtrated and reduced under reduced pressure. The obtained crude product is purified via recrystallization using toluene as solvent, giving E3 as solid.
59% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; water; at 110.0℃;Inert atmosphere; E1 (1.00 equivalents), E2 (1 .15 equivalents), Pd(dppf)Cl2 (0.05 equivalents) and potassium acetate (2.50 equivalents) are stirred under nitrogen atmosphere in a mixture of dioxane and water (10: 1 ) at 1 10 C until completion of the reaction (monitoring with GC/MS, usually finished within 4-24 h). Active carbon and Celite are added to the reaction mixture and stirred at 100 C for 10 minutes. Subsequently, the mixture is hot filtered and concentrated under reduced pressure. The residue is dissolved in dichloromethane and washed with water and brine. The organic phase is dried with MgS04, filtrated and reduced under reduced pressure. The obtained crude product is purified via recrystallization using toluene as solvent, yielding E3 as a solid. AAV2 (59% yield), wherein 4-chloro-2,6-diphenylpyrimidine (CAS 29509-91-9) was used as reactant.
  • 15
  • [ 1092485-88-5 ]
  • C58H35FN2O2 [ No CAS ]
  • 16
  • [ 1092485-88-5 ]
  • C76H45N3O3 [ No CAS ]
  • 17
  • [ 1092485-88-5 ]
  • [ 2915-16-4 ]
  • C22H13Cl2FN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In tetrahydrofuran; water; at 2080.0℃; for 20.0h;Inert atmosphere; General procedure: <strong>[1092485-88-5]3,5-dichloro-4-fluorophenyl boronic ester</strong> (1.00 equivalents; CAS 1092485-88-5), 2-chloro-4,6-diphenyl-1,3,5-triazine (1.1 equivalents), Pd(dppf)2Cl2 (0.05 equivalent), and potassium acetate (3.00 equivalents) are stirred under nitrogen atmosphere in a THF/water mixture (ratio of 10:1) at 80 C. for 20 h. The cooled mixture is poured into brine, the precipitated product is filtered off and washed with water and cold ethanol. The product E1-1 is obtained as a solid.
  • 18
  • [ 1092485-88-5 ]
  • [ 3842-55-5 ]
  • C21H12Cl2FN3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In tetrahydrofuran; water; at 2080.0℃; for 20.0h;Inert atmosphere; <strong>[1092485-88-5]3,5-dichloro-4-fluorophenyl boronic ester</strong> (1.00 equivalents; CAS 1092485-88-5), 2-chloro-4,6-diphenyl-1,3,5-triazine (1.1 equivalents), Pd(dppf)2Cl2 (0.05 equivalent), and potassium acetate (3.00 equivalents) are stirred under nitrogen atmosphere in a THF/water mixture (ratio of 10:1) at 80 C. for 20 h. The cooled mixture is poured into brine, the precipitated product is filtered off and washed with water and cold ethanol. The product E1-1 is obtained as a solid.
 

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