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Chemical Structure| 1009033-87-7 Chemical Structure| 1009033-87-7

Structure of 1009033-87-7

Chemical Structure| 1009033-87-7

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Product Details of [ 1009033-87-7 ]

CAS No. :1009033-87-7
Formula : C17H20BNO2
M.W : 281.16
SMILES Code : CC1(C)OB(OC1(C)C)C1=CC=C(C=C1)C1=CC=NC=C1
MDL No. :MFCD12828171
InChI Key :PTNMCYWJKRZCDE-UHFFFAOYSA-N
Pubchem ID :58526497

Safety of [ 1009033-87-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 1009033-87-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 21
Num. arom. heavy atoms 12
Fraction Csp3 0.35
Num. rotatable bonds 2
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 86.15
TPSA ?

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

31.35 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

3.46
Log Po/w (WLOGP)?

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

3.05
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.

1.89
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

2.9
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.26

Water Solubility

Log S (ESOL):?

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

-4.05
Solubility 0.0248 mg/ml ; 0.0000883 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.

-3.8
Solubility 0.0446 mg/ml ; 0.000158 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

-6.14
Solubility 0.000205 mg/ml ; 0.000000728 mol/l
Class?

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

Poorly 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

Yes
Log Kp (skin permeation)?

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

-5.56 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)

2.87

Application In Synthesis of [ 1009033-87-7 ]

* 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 [ 1009033-87-7 ]

[ 1009033-87-7 ] Synthesis Path-Downstream   1~30

  • 1
  • [ 1009033-87-7 ]
  • [ 16400-50-3 ]
  • [ 1009033-98-0 ]
  • 2
  • [ 39795-60-3 ]
  • [ 73183-34-3 ]
  • [ 1009033-87-7 ]
YieldReaction ConditionsOperation in experiment
100% A 100 mL sealed tube was charged with 4-(4-bromophenyl)pyridine (0.9 g, 3.8mmol), bis(pinacolato)diboron (1.17 g, 4.61 mmol), potassium acetate (0.745 g, 7.6mmol) and 1-4 dioxane (10 mL). The reaction mixture was purged with argon for 30mm. Then, Pd(dppf)C12 (0.75 g, 0.05 eq) was added and heated at 100 00 over night.After cooing, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous Na2SO4. The organic layer was concentrated under vacuo to yield crude product, which was purified by combif lash to yield title compound (1.0 g, 100.0percent). LCMS: (M+H) = 282.1
  • 3
  • [ 1009033-87-7 ]
  • [ 1228585-13-4 ]
  • [ 1228585-25-8 ]
YieldReaction ConditionsOperation in experiment
61% With caesium carbonate;palladium diacetate; XPhos; In tetrahydrofuran; for 22h;Inert atmosphere; Reflux; In a stream of argon, 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)phenyl]pyridine (420 mg), 2,4-bis(5-chlrobiphenyl-3-yl)-6-phenyl-1,3,5-triazine (263 mg), cesium carbonate (485 mg), palladium acetate (5.6 mg) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (23.7 mg) were suspended in tetrahydrofuran (15 mL), and the suspension was refluxed for 22 hours. The reaction mixture was left to stand at room temperature, and then low-boiling ingredients were distilled away under a reduced pressure. Methanol was added to the obtained solid. The solid precipitate was recovered by filtration, and the obtained crude product was purified by silica gel chromatography using a methanol/chloroform (1:100 - 1:50) mixed liquid as a developing solvent to give 232 mg of the target 6-phenyl-2,4-bis[4-(4-pyridyl)-1,1':3',1'-terphenyl-5'-yl]-1,3,5-triazine as a white powder (yield: 61%). 1H-NMR (CDCl3) :delta7.49(brt,J=7.1Hz,2H) 7.57(d,J=7.5Hz, 4H), 7.61-7.66(m,7H),7.82-7.86(m,8H),7.94(d,J=8.5Hz,4H),8.10(t,J= 1.7Hz,2H),8.73(dd,J=4.5,1.6Hz,4H),8.84(brdd,J=7.7,1.7Hz,2H), 9.04(d,J=1.7Hz,4H). 13C-NMR(CDCl3) :delta121.5(CH*4),126.5(CH*2) ,127.1(CH*2) ,127.4 (CH*4),127.6(CH*4),127.9(CH*2),128.1(CH*4),128.7(CH*2),129.0 (CH*4),129.1(CH*2),130.0(CH*2),132.8(CH),136.1(quart.),137.5 (quart.*2),137.6(quart.*2),140.7(quart.*2),141.4(quart.*2), 141.6(quart.*2),142.6(quart.*2),147.8(quart.*2),150.4(CH*4), 171.8(quart.*2),171.9(quart.).
  • 4
  • [ 1009033-87-7 ]
  • [ 1312478-57-1 ]
  • [ 1358778-93-4 ]
  • 5
  • [ 1009033-87-7 ]
  • [ 1268250-67-4 ]
  • [ 1268250-68-5 ]
YieldReaction ConditionsOperation in experiment
58% With caesium carbonate; XPhos;palladium diacetate; In tetrahydrofuran; for 87h;Inert atmosphere; Reflux; In a stream of argon, 0.40 g (0.81 mmol) of 2-(3,5-dibromophenyl)-4,6-di-p-tolylpyrimidine, 0.48 g (1.70 mmol) of 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)phenyl]-pyridine, 0.55 g (1.70 mmol) of cesium carbonate, 7 mg (0.032 mmol) of palladium acetate and 31 mg (0.065 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl were suspended in 20 mL of tetrahydrofuran, and the obtained suspension was heated under reflux for 87 hours. The reaction mixture was cooled to room temperature, and was then distilled under a reduced pressure to remove all volatile materials. Methanol was added to the concentrate and the thus-deposited solid was collected by filtration. The thus-obtained crude product was purified by silica gel chromatography using a chloroform/methanol (100:1) mixed solvent as an eluent to give 0.30 g of the target 2-[4,4"-di(4-pyridyl)-1,1' :3',1"-terphenyl- 5'-yl]-4,6-di-p-tolylpyrimidine as a white solid (yield: 58%). 1H-NMR(CDCl3):delta2.50(s,6H),7.41(d,J=8.0Hz,4H),7.63(dd,J=4.5, 1.5Hz,4H),7.84(d,J=8.3Hz,4H),7.95(d,J=8.3Hz,4H),8.03(t,J=1.8Hz, 1H),8.05(s,1H),8.24(d,J=8.0Hz,4H),8.73(dd,J=4.5,1.5Hz,4H),9.02(d, J=1.8Hz,2H). 13C-NMR(CDCl3):delta21.6(CH3),31.0(CH3),110.1(CH),121.5(CH×4), 126.7(CH×2),127.3(CH×4),127.5(CH×4),128.2(CH×4),129.7(CH×4),134.7 (quart.×2),137.3(quart.×2),139.9(quart.),141.2(quart.×2),141.3 (quart.×2),142.0(quart.×2),147.9(quart.×2),150.4(CH×4), 164.0(quart.),164.7(quart.×2).
  • 6
  • [ 1009033-87-7 ]
  • [ 1407504-40-8 ]
  • [ 1383795-51-4 ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 90℃; for 12h; 15.0 g (32.2 mmol) of the intermediate product (N), 10.9 g (38.6 mmol) of <strong>[1009033-87-7]4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine</strong>, and 1.1 g (1.0 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 300 mL of a tetrahydrofuran (THF) solvent. A solution in which 8.9 g (64.4 mmol) of potassium carbonate (K2CO3) was dissolved in 100 ml of water was added thereto, and they were reacted at 90 C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residues were recrystallized with toluene, precipitated crystals were separated by a filter, rinsed with toluene, and dried to provide a white solid of a compound in 17.0 g (yield: 90%). (calculation value: 584.71, measurement value: MS[M+1] 585.01)
  • 7
  • [ 1009033-87-7 ]
  • [ 1407504-43-1 ]
  • [ 1407503-02-9 ]
YieldReaction ConditionsOperation in experiment
64% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 90℃; for 12h; 20.0 g (23.6 mmol) of the intermediate product (N), 18.1 g (64.4 mmol) of <strong>[1009033-87-7]4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine</strong>, and 1.5 g (1.3 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolved in 400 ml of a tetrahydrofuran (THF) solvent. A solution in which 11.9 g (85.8 mmol) of potassium carbonate (K2CO3) was dissolved in 200 ml of water was added thereto, and then they were reacted at 90 C. for 12 hours. The solvent was removed under a reduced pressure, and the reaction product was rinsed with water and methanol. The residues were recrystallized with toluene, precipitated crystals were separated by a filter, rinsed with toluene, and dried to provide a white solid of a compound in 16.0 g (yield: 64%). (calculation value: 584.71, measurement value: MS[M+1] 585.01)
YieldReaction ConditionsOperation in experiment
General procedure: Step-ii: 1-(2-fluorobenzyl)-4-( 4,4,5 ,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1 H-pyrazole1-(2-fluorobenzyl)-4-iodo-1H-pyrazole (2.25 g, 7.4 mmol) and bispinocalatodiboron (2.07 g,8.2 mmol) were added to a solution of DMSO (20 ml) previously purged with argon (10min). The reaction mixture was purged with argon for a further 15mins, followed by the10 addition of potassium acetate (2.19 g, 22.3 mmol) andbis(triphenylphosphine)palladium(II)dichloride (261 mg, 0.3725 mmol). The resultingmixture was heated to reflux at 80 oc overnight. The reaction was monitored by TLC (40%ethyl acetate in hexane). The reaction mixture was cooled and diluted with ethyl acetate (100ml) and filtered over celite bed and the filtrate was washed with cold water (2x100 ml). The15 organic layer was dried over NazS04, and concentrated under reduced pressure to afford 2.3 gof the crude product which was taken as such for next reaction.
  • 9
  • [ 1009033-87-7 ]
  • [ 1450642-87-1 ]
  • [ 1534378-91-0 ]
YieldReaction ConditionsOperation in experiment
70.5% Using similar reaction conditions as described in step-ii of example-1, 5-bromo-3-(1-(3-5 fluorobenzyl)-3,5-dimethyl-1 H-pyrazol-4-yl)-l-tosyl-1H-pyrrolo[2,3-b] pyridine (step-i ofexample-14) (150mg, 0.27mmol) was coupled with <strong>[1009033-87-7]4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine</strong> (intermediate 45) (91.44mh, 0.32mmol) in sodiumcarbonate (85.86, 0.81mmol), toluene/ethanol/water (5/5/2ml). This afforded 120mg (70.5%yield) of the titled compound.
  • 10
  • [ 106-37-6 ]
  • [ 1009033-87-7 ]
  • 12
  • [ 1009033-87-7 ]
  • 5-bromo-6-chloro-1,3-dihydro-2H-indol-2-one [ No CAS ]
  • 6-chloro-5-[4-(pyridin-4-yl)phenyl]-1,3-dihydro-2H-indol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
18.1% A 100 mL sealed tube charged with intermediate 37 (1 .0 g, 3.5 mmol), intermediate 3(0.86 g, 3.1 mmol), potassium phosphate tribasic (2.0 g, 10.5 mmol), 1, 4-dioxane (10mL) and water (3 mL) was degassed with nitrogen for 15 mm. To the above solutionPd(PPh3)4 (0.2 g, 0.05 eq) was added and heated at 100 00 over night. After cooling,the reaction mixture was diluted with water and extracted by using ethyl acetate. The combined organic layer was dried and concentrated. The product was purified by combi-flash to yield title compound (0.2 g, 18.1%) as a brown solid. LOMS: (M+H) = 321.0;1H NMR: (DMSO-d6, 300MHz) 610.61(s, 1H), 8.66- 8.67(d, 2H), 7.88-7.91(d,2H), 7.77- 7.78 (d, 2H), 7.53-7.56 (d, 2H), 7.30 (5, 1 H), 6.97 (5, 1 H), 3.54 (5, 2H).
  • 13
  • [ 1009033-87-7 ]
  • 5-bromo-6-fluoro-1,3-dihydro-2H-indol-2-one [ No CAS ]
  • 6-fluoro-5-[4-(pyridin-4-yl)phenyl]-1,3-dihydro-2H-indol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% A microwave vial was charged with intermediate 1(0.2 g, 0.9 mmol), intermediate 37(0.24 g, 0.9 mmol) and DMF: 1 ,4-Dioxane: water (2 mL: 0.5 mL: 0.5 mL) mixture. To the above solution potassium phosphate (tribasic) (0.55 g, 1 .8 mmol) was added and the vial was degasified for 15 mm after which Pd(PPh3)4 (0.05 g, 0.03 eq) was added and heated at 150 00 for 30 mm. After cooling, the reaction mixture diluted with water and extracted by using ethyl acetate. The combined organic layer was dried andconcentrated. The product was purified by chromatography to yield title compound (0.075 g, 27.0%) as a brown solid. LCMS: (M+H) = 305.1
  • 14
  • [ 1193-21-1 ]
  • [ 1009033-87-7 ]
  • [ 181219-01-2 ]
  • C20H14N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% <a> Synthesis of Intermediate (44- 1) A flask was charged with 4,6-dichloropyridine (596 mg, 4.0 mmol), followed by being purged with argon gas. To the flask, thereafter, dioxane (60 mL), which had been deaerated with argon gas, 4-(4-pyridyl)phenyl boronic acid pinacol ester (4.0 mmol, 2.26 g), bis(triphenylphosphine) palladium(II) dichloride (0.3 mmol, 210 mg) were added. After bubbling the solution with argon gas, 2M K2CO3 (20 mL) was added, and the resultant was heated and stirred at 50C for 4 hours. Subsequently, 4-(4,4, 5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)pyridine (4 mmol, 820 mg) was added, and the resulting mixture was heated and stirred at 100C for 4 hours. The resultant was filtered with Celite, and water and chloroform were added to the filtrate to separate an organic layer. Thereafter, a water layer was extracted 5 times with chloroform. The combined organic layer was washed with saturated salt water, followed by drying with sodium sulfate to condensate the filtrate, to thereby obtain a crude product. The crude product was purified by silica-gel column chromatography (eluenf- chloroform/methanol = 93/7), and the obtained solids were dispersed and washed in chloroform/hexane. The solids were collected by filtration, and the obtained solids were vacuum dried to thereby obtain an intermediate (44- 1) as pale yellow solids (the yielded amount: 892 mg, the yield: 72%). NMR (500 MHz, CDCI3, delta) : 9.42 (d, J = 1.7 Hz, 1H), 8.85(dd, Ji = 5.8 Hz, J2 = 1.8 Hz, 2H), 8.73(dd, Ji = 6.3 Hz, J2 = 1.7 Hz, 2H), 8.31 (d, J =8.6 Hz, 2H), 8.2l(d, J = 1.7 Hz, 1H), 8.04 (dd, Ji = 6.3 Hz, J2 = 1.7 Hz, 2H), 7.84 (d, J =6.9 Hz, 2H), 7.59 (d, Ji = 5.8 Hz, J2 = 1.8 Hz, 2H)
  • 15
  • [ 3764-01-0 ]
  • [ 1009033-87-7 ]
  • [ 181219-01-2 ]
  • C31H21N5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% <a> Synthesis of Intermediate (80- 1) Intermediate (80" l) A flask was charged with 2,4,6-trichloropyridine (732 mg, 4.0 mmol), followed by being purged with argon gas. To the flask, thereafter, dioxane (60 niL), which had been deaerated with argon gas, 4-(4-pyridyl)phenyl boronic acid pinacol ester (8.0 mmol, 2.26 g), and bis(triphenylphosphine)palladium(II) dichloride (0.3 mmol, 210 mg) were added. After bubbling the solution with argon gas, 2M K2CO3 (20 mL) was added, and the resultant was heated and stirred at 50C for 4 hours. Next, 4-4,4, 5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)pyridine (4 mmol, 820 mg) was added and the resultant was heated and stirred at 100C for 4 hours. Subsequently, the resultant was filtered with Celite, and water and chloroform were added to the filtrate to separate an organic layer. Thereafter, a water layer was extracted 5 times with chloroform. The combined organic layer was washed with saturated salt water, followed by drying with sodium sulfate to condensate the filtrate, to thereby obtain a crude product. The crude product was purified by silica-gel column chromatography (eluent: chloroform/methanol = 93/7), and the obtained solids were dispersed and washed in chloroform/hexane. The solids were collected by filtration, and the obtained solids were vacuum dried to thereby obtain an intermediate (80- 1) as pale yellow solids (the yielded amount: 1.19 g, the yield: 64% H NMR (500 MHz, CDCI3, delta) : 8.87 (dd, Ji = 4.7 Hz, J2 = 1.7 Hz, 2H), 8.75 (dd, Ji = 4.0 Hz, J2 = 1.7 Hz, 4H), 8.58 (dd, Ji = 4.7 Hz, J2 = 1.7 Hz, 2H), 8.45 (dt Ji = 8.0 Hz, J2 = 1.7 Hz, 4H), 8.21 (s, 1H), 7.88 (dd, Ji = 8.6 Hz, J2 = 1.7 Hz, 4H), 7.61 (dd, Ji = 4.7 Hz, J2 = 1.7 Hz, 4H)
61% 2, 4, 6-trichloropyrimidine (732 mg, 4.0 mmol) was placed in a flask,After substitution with argon gas,Dioxane (60 mL) degassed with argon gas,4- (4-pyridyl) phenylboronic acid pinacol ester (8.0 mmol, 2.26 g) represented by the following structural formula (28)Bis (triphenylphosphine) palladium (II) dichloride (0.3 mmol, 210 mg) was added.After bubbling the solution with argon gas,2 M K 2 CO 3 (20 mL) was added,And the mixture was heated and stirred at 50 C. for 4 hours.Then 4- (4,4,5,5-tetramethyl-1,3,2-dioxeSabololan-2-yl) pyridine(4 mmol, 820 mg) was added,And the mixture was heated and stirred at 100 C. for 4 hours.Subsequently, the contents were filtered through celite, water and chloroform were added to the filtrate to separate the organic layer,The aqueous layer was extracted with chloroform.The combined organic layer was dried over sodium sulfate and the filtrate was concentrated to give a crude product.This was purified by silica gel chromatography (developing solvent: chloroform / methanol)The solid obtained after the concentration was dried under vacuum,The target compound was obtained as a pale yellow solid (yield 1.13 g, yield 61%).
  • 16
  • [ 108-77-0 ]
  • [ 1009033-87-7 ]
  • 2,4,6-tris<4-(4-pyridyl)phenyl>-1,3,5-triazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 1,4-dioxane; water; at 20 - 50℃; for 30h;Inert atmosphere; <a> Synthesis of Intermediate (9- 1) Intermediate (9- 1) A flask was charged with 3.0 g of 2,4,6-trichloro- l,3, 5-triazine, and was purged with argon gas. To the flask, thereafter, dioxane (100 mL), phenylpyridine boronic acid pinacol ester (18.5 g), and PdCl2(PPh3)2 (600 mg) were added. To the mixture, 2M K2CO3 (17 mL) was added, and the resulting mixture was stirred for 14 hours at 50C, followed by stirring for 16 hours at room temperature. The resultant was filtered with Celite, and water and chloroform were added to the filtrate to separate an organic layer. Thereafter, a water layer was extracted 3 times with chloroform. The combined organic layer was washed with saturated salt water, followed by drying with sodium sulfate to condensate the filtrate, to thereby obtain a crude product (the yielded amount: 7.5 g) . The crude product was purified by silica-gel column chromatography (eluent^ CHC methanol = 93/7), and the obtained solids were dispersed and washed in chloroform/hexane. The solids were collected by filtration, and the obtained solids were vacuum dried to thereby obtain a target (the yielded amount: 6.9 g, the yield'- 78%) as white solids.
  • 17
  • [ 1009033-87-7 ]
  • C28H16Cl2N2 [ No CAS ]
  • C50H32N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 90℃; for 12h; 20.0 g (44.3 mmol) of the intermediate product (F), 29.9 g (106.4 mmol) of <strong>[1009033-87-7]4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine</strong> and 2.6 g (2.2 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolvedin 400 ml of tetrahydrofuran (THF) as a solvent, a solution obtained by dissolving 24.5 g (177.3 mmol) of potassiumcarbonate (K2CO3) in 200 ml of water was added thereto, and the mixture was reacted at 90 C for 12 hours. A crystalformed therein was separated with a filter and washed with water and methanol. The residue was recrystallized withchloroform, and the precipitated crystal was separated with a filter, washed with methanol and dried, obtaining 20.0 gof a yellow solid compound (a yield: 66 %). (calculation value: 688.82, measurement value: MS[M+1] 689.12)
  • 18
  • [ 607-68-1 ]
  • [ 1009033-87-7 ]
  • C30H20N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 90℃; for 12h; 10.0 g (50.2 mmol) of 2,4-dichloroquinazoline, 31.1 g (110.5 mmol) of <strong>[1009033-87-7]4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine</strong> and 2.9 g (2.5 mmol) of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] were dissolvedin 200 ml of tetrahydrofuran (THF) as a solvent, a solution obtained by dissolving 27.8 g (200.9 mmol) of potassiumcarbonate (K2CO3) in 100 ml of water was added thereto, and the mixture was reacted at 90 C for 12 hours. Afterremoving the solvent under a reduced pressure, the obtained reactant was washed with water and methanol. The residuewas recrystallized with toluene, and the precipitated crystal was separated with a filter, washed with methanol and dried,obtaining 15.0 g of a white solid compound (a yield: 68 %). (calculation value: 436.51, measurement value: MS[M+1]436.86)
  • 19
  • [ 1193-21-1 ]
  • [ 1009033-87-7 ]
  • C26H18N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 1,4-dioxane; at 100℃; for 8h;Inert atmosphere; 4,6-Dichloropyrimidine (1.49 g, 10 mmol) was placed in a flask, and after substitution with argon gas, dioxane (120 mL) degassed with argon gas,4- (4-pyridyl) phenylboronic acid pinacol ester (20 mmol, 5.6 g),Bis (triphenylphosphine) palladium (II) dichloride (0.2 mmol, 140 mg) was added.After bubbling the solution with argon gas, 2 M aqueous potassium carbonate solution (40 mL) was added,And the mixture was heated and stirred at 100 C. for 8 hours.The contents were filtered through celite, water and chloroform were added to the filtrate to separate the organic layer, and the aqueous layer was extracted with chloroform.The combined organic layer was dried over sodium sulfate and the filtrate was concentrated to give a crude product.This was purified by silica gel chromatography (developing solvent: chloroform / methanol), the obtained solid was washed with chloroform / hexane, and the solid collected by filtration was vacuum-dried to obtain the desired product as a pale yellow solid (yield 1 .58 g, yield 41%).
  • 20
  • [ 3764-01-0 ]
  • [ 1009033-87-7 ]
  • C26H17ClN4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In toluene; at 50℃; for 5h;Inert atmosphere; In a flask, 1.83 g of 2,4,6-trichloropyrimidine, 5.65 g of the boronic acid ester shown in the above scheme (1), and 0.35 g of dichlorobis (triphenylphosphine) palladium were placed and purged with argon.100 ml of toluene and 20 ml of 2 M potassium carbonate aqueous solution were added and stirred at 50 C. for 5 hours.The reaction solution was washed with an aqueous sodium chloride solution and then purified by column chromatography to obtain a colorless solid.Yield 40%.Further, the obtained solid was stirred with triple molar amount of bromooctylphosphonic acid in the presence of DMF solvent at 90 C. for 4 hours to obtain (actual -1) as a colorless solid.Yield 60%.
  • 21
  • [ 1009033-87-7 ]
  • [ 1433887-06-9 ]
  • [ 2926-30-9 ]
  • C20H26BN2O5S(1+)*CF3O3S(1-) [ No CAS ]
  • 22
  • [ 1009033-87-7 ]
  • [ 117635-22-0 ]
  • C44H52N2 [ No CAS ]
  • 23
  • [ 1009033-87-7 ]
  • [ 21521-51-7 ]
  • C50H34N4 [ No CAS ]
  • 24
  • [ 1009033-87-7 ]
  • C24H12Br2N4 [ No CAS ]
  • C46H28N6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.6 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 18h;Inert atmosphere; Reflux; The specific operation process is: in a 100mL three-necked flask,Compound D02 (2.06 g, 0.004 mol) was added.Compound E08 (2.24 g, 0.008 mol),Potassium carbonate (1.1 g, 0.008 mol), toluene (46 g), deionized water (25 g),Under the protection of nitrogen, the catalyst Pd(PPh3)4 (0.18g) was added.The temperature is raised to reflux, the reaction is kept for 18 hours, the temperature is lowered to 40 C, and the liquid is separated.The aqueous phase was extracted once with 50 mL of tetrahydrofuran, and the organic phases were combined.The solvent is removed, and the obtained crude product is purified by silica gel column chromatography.The eluent is dichloromethane: petroleum ether = 1:1 (volume ratio),Obtained the target product C15 crude 1.9g,Further sublimation purification using a chemical vapor deposition system, sublimation temperature 365 C,Obtained 1.6g target C15,
  • 25
  • [ 1009033-87-7 ]
  • [ 24424-99-5 ]
  • C22H40BNO4 [ No CAS ]
  • C22H40BNO4 [ No CAS ]
  • 26
  • [ 1009033-87-7 ]
  • C86H82Br4N8O4 [ No CAS ]
  • C130H114N12O4 [ No CAS ]
  • 27
  • [ 1009033-87-7 ]
  • C94H98Br4N8O4 [ No CAS ]
  • C138H130N12O4 [ No CAS ]
  • 28
  • [ 1009033-87-7 ]
  • [ 61326-44-1 ]
  • 1,1,2,2-tetrakis(4'-(pyridin-4-yl)-[1,1'-biphenyl]-4-yl)ethene [ No CAS ]
  • 29
  • [ 1009033-87-7 ]
  • 8-(3-bromo-5-chloropyridin-4-yl)-2,8-diazaspiro[4.5]decan-1-one [ No CAS ]
  • 8-[3-chloro-5-(4-pyridin-4-ylphenyl)pyridin-4-yl]-2,8-diazaspiro[4.5]decan-1-one [ No CAS ]
  • 30
  • [ 589-87-7 ]
  • [ 1009033-87-7 ]
 

Historical Records

Technical Information

Categories

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[ 1009033-87-7 ]

Organoborons

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A806030 [144432-80-4]

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Related Parent Nucleus of
[ 1009033-87-7 ]

Pyridines

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