Structure of 129013-83-8
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CAS No. : | 129013-83-8 |
Formula : | C11H8BrN |
M.W : | 234.09 |
SMILES Code : | BrC1=CC=C(C2=CC=CN=C2)C=C1 |
MDL No. : | MFCD04116232 |
InChI Key : | FCHUOBPHXDXZBK-UHFFFAOYSA-N |
Pubchem ID : | 1515241 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 57.37 |
TPSA ? Topological Polar Surface Area: Calculated from |
12.89 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.32 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.17 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.51 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.82 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.7 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.1 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.91 |
Solubility | 0.0291 mg/ml ; 0.000124 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.11 |
Solubility | 0.181 mg/ml ; 0.000774 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.4 |
Solubility | 0.00093 mg/ml ; 0.00000397 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
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) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.48 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.78 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48.5 g | With sulfuric acid; bromine; silver sulfate; at 20℃; for 4h; | Compound 1 50.0g (0.32mol) was added 150mL of concentrated sulfuric acid, and added Ag2SO4(50.0g0.16mol), liquid bromine (51.2g, 0.32mol) was slowly added dropwise to the reaction mixture, after the addition was complete, the reaction at room temperature for 4 hours, the insoluble was filtered off, the filtrate was slowly added to 300mL ice-water mixture, and continued stirring, solid precipitated solid was filtered off, dried in vacuo at 45 , pale yellow 48.5g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In DMF (N,N-dimethyl-formamide); water; at 85℃; for 1h; | A mixture of the boronate from Step 1,<strong>[129013-83-8]3-(4-bromophenyl)pyridine</strong> from Step 2 (1.5 eq), [1,1'-bis (diphenylphosphino)ferrocene]dichloropalladium(II) (0.05 eq) and 2M aqueous sodium carbonate (5 eq) in N,N-dimethylformamide (7 ml/mmol) was stirred at 85 C. for 1 hour. After cooling, the mixture was partitioned between ethyl acetate and water. The crude product from the organic phase was chromatographed on silica gel eluting with a 7:3 mixture of ethyl acetate and methylene chloride to afford the N-Isopropyl-1-{3-[4-(pyridin-3-yl)phenyl]phenyl}-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide compound as a solid. 1H NMR (CDCl3) delta 1.30 (d, 6H), 4.25 (m, 1H), 7.35 (m, 1H), 7.39-7.48 (m, 2H), 7.60-7.75 (m, 6H), 7.80 (d, 1H), 7.90 (d, 1H), 8.58 (d, 1H), 8.70 (m, 1H), 8.82 (d, 1H), 8.88 (s, 1H), 9.08 (s, 1H), 9.68 (br, NH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In DMF (N,N-dimethyl-formamide); water; at 85℃; for 4h; | A mixture of pyridine-3-boronic acid 1,3-propanediol cyclic ester, 4-bromoiodobenzene (1.1 eq), [1,1'-bis (diphenylphosphino)ferrocene]dichloropalladium(II) (0.05 eq) and 2M aqueous sodium carbonate (5 eq) in N,N-dimethylformamide (2 ml/mmol) was stirred at 85 C. for 4 hours. After quenching with saturated aqueous ammonium chloride solution, the mixture was partitioned between ethyl acetate and water, and the crude product from the organic phase was chromatographed on silica gel eluting with a 1:9 mixture of ethyl acetate and hexane to afford the 3-(4-Bromophenyl)pyridine compound as a solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; | Step 3 N-Isopropyl-1-{3-[4-(Pyridin-3-yl)Phenyl]Phenyl}-1,4-Dihydro[1,8]Naphthyridin-4-One-3-Carboxamide A mixture of the boronate from Step 1, <strong>[129013-83-8]3-(4-bromophenyl)pyridine</strong> from Step 2 (1.5 eq), [1,1'-bis (diphenylphosphino)ferrocene]dichloropalladium(II) (0.05 eq) and 2M aqueous sodium carbonate (5 eq) in N,N-dimethylformamide (7 ml/mmol) was stirred at 85° C. for 1 hour. After cooling, the mixture was partitioned between ethyl acetate and water. The crude product from the organic phase was chromatographed on silica gel eluding with a 7:3 mixture of ethyl acetate and methylene chloride to afford the N-Isopropyl-1-{3-[4-(pyridin-3-yl)phenyl]phenyl}-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide compound as a solid. 1H NMR (CDCl3) delta 1.30 (d, 6H), 4.25 (m, 1H), 7.35 (m, 1H), 7.39-7.48 (m, 2H), 7.60-7.75 (m, 6H), 7.80 (d, 1H), 7.90 (d, 1H), 8.58 (d, 1H), 8.70 (m, 1H), 8.82 (d, 1H), 8.88 (s, 1H), 9.08 (s, 1H), 9.68 (br, NH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In hexane; ethyl acetate; N,N-dimethyl-formamide; | Step 2 3-(4-Bromophenyl)Pyridine A mixture of pyridine-3-boronic acid 1,3-propanediol cyclic ester, 4-bromoiodobenzene (1.1 eq), [1,1'-bis (diphenylphosphino)ferrocene]dichloropalladium(II) (0.05 eq) and 2M aqueous sodium carbonate (5 eq) in N,N-dimethylformamide (2 ml/mmol) was stirred at 85° C. for 4 hours. After quenching with saturated aqueous ammonium chloride solution, the mixture was partitioned between ethyl acetate and water, and the crude product from the organic phase was chromatographed on silica gel eluding with a 1:9 mixture of ethyl acetate and hexane to afford the 3-(4-Bromophenyl)pyridine compound as a solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In hexane; ethyl acetate; N,N-dimethyl-formamide; | Step 1: 3-(4-Bromophenyl)pyridine. A mixture of pyridine-3-boronic acid 1,3-propanediol cyclic ester, 4-bromoiodobenzene (1.1 eq), [1,1'-bis (diphenylphosphino)ferrocene]dichloropalladium(II) (0.05 eq) and 2M aqueous sodium carbonate (5 eq) in N,N-dimethylformamide (2 mL/mmol) was stirred at 85° C. for 4 hours. After quenching with saturated aqueous ammonium chloride solution the mixture was partitioned between ethyl acetate and water and the crude product from the organic phase was chromatographed on silica gel eluding with a 1:9 mixture of ethyl acetate and hexane to afford the 3-(4-bromophenyl)pyridine compound as a solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With magnesium;copper(I) chloride; In tetrahydrofuran; | a) 3,3(2,2-Dimethyltrimethylenedioxy)-11beta-[4-(3-pyridyl)phenyl]-9-estrene-5alpha,17beta-diol (61) 10.6 g of above compound 61 is obtained, as described under example 2a), from 3.57 g of magnesium chips in 150 ml of absolute tetrahydrofuran, 3.2 g of 1-bromo-4-(3-pyridyl)-benzene [preparation following example 14] in 100 ml of absolute tetrahydrofuran, 380 mg of copper(I) chloride and 10.0 g of 5alpha,10alpha-epoxy-3,3(2,2-dimethyltrimethylenedioxy)-9(11)-estren-17-ol in 80 ml of absolute tetrahydrofuran. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | The 4-(pyrid-4-yl)bromobenzene used as starting material was prepared using the procedure described in Example 1(b) for the preparation of 4-(pyrid-3-yl)bromobenzene, but using 4-bromopyridine in place of 3-bromopyridine. There was thus obtained 4-(4-bromophenyl)pyridine as a solid (31percent yield), m.p. 123°-124° C.; microanalysis, found: C, 56.4; H, 3.4; N, 5.9percent; C11 H8 NBr requires: C, 56.4; H, 3.4; N, 6.0percent; NMR([CD3 ]2 SO): 7.65-7.8(6H, m) and 8.65-8.70(2H,m); m/z 235(M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The 2-(4-bromophenyl)pyridine used as starting material was obtained using the procedure described in Example 1 for the preparation of 3-(4-bromophenyl)pyridine, but using 2-bromopyridine in place of 3-bromopyridine. There was thus obtained 2-(4-bromophenyl)pyridine as an oil, NMR (CDCl3): 7.25(1H, m), 7.6(2H, d), 7.7-7.8(2H, m), 7.9(1H, d), 8.5(1H, d of d). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.0% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 1.5h;Inert atmosphere; Reflux; | In a 1000 ml reaction flask, with mechanical stirring, Ar gas protection, adding 10. 01g (molecular weight 282,0 · 0355 mol), pyridine -3-boric acid 4 · 37 g (molecular weight 123, 0.0355 mol), catalyst Pd (PPh3) 4 dosage 2 · 14g (molecular weight 1154, 0.00185mol), sodium carbonate aqueous solution 200ml (2M), toluene 200ml, ethyl 200ml. The mixture was stirred under reflux and the reaction was monitored by TLC. After 1.5 hrs of reaction, the plate was found and the reaction was found to be complete. It was cooled, extracted with ethyl acetate, evaporated to dryness and purified by column chromatography. The eluent was petroleum ether: ethyl acetate = 20:1 (V1/V2), yielding white solid 7.73 g, molecular weight 232, HPLC at 98.1% yield: 92.0% |
56% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 5h;Inert atmosphere; Heating; | In the three-necked flask, Join p-Bromoiodobenzene (28g, 0.1mol),3-pyridyl boronic acid (12.3g, 0.1mol),Potassium carbonate (27.2g, 200mmol),Tetrakistriphenylphosphine palladium (0.8g),Tetrahydrofuran (200ml) and water (50ml),Heated under a nitrogen atmosphere for 5 hours.cool down,filter,The crude product was purified by column chromatography to give the product 13g,Yield 56%. |
38% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; water; at 80℃; for 12h; | A synthetic scheme of 3- (4-broniophenyl)pyridine is shown in (C-1). In a 100 mL three-necked flask were placed 2.4 g (20 mmol) of 3-pyridineboronic acid, 5.6 g (19 mmol) of para-bromoiodobenzene, and 4.5 g (42 mmol) of sodium carbonate. The atmosphere in the flask was replaced with nitrogen, and to the flask were added 15 mL of water, 25 mL of DME, and 10 mL of ethanol. The mixture was degassed by being stirred under reduced pressure, to which 0.22 g (0.19 mmol) of tetrakis(triphenylphosphine)palladium(0) was added. The mixture was stirred under nitrogen stream at 80 C for 12 hours. After a predetermined time, water was added to the mixture, and an organic substance was extracted with chloroform from the aqueous layer. The obtained extract was washed with a saturated aqueous sodium chloride solution together with the organic layer and then dried over magnesium sulfate. The mixture was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and the filtrate was condensed to obtain an oily substance. The obtained substance was purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1); thus, 1.8 g of the target yellow oily substance was obtained with a yield of 38 %. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With sodium carbonate;palladium diacetate; tris-(o-tolyl)phosphine; In 1,2-dimethoxyethane; water; at 80℃; for 10h; | A synthetic scheme of PPy1PQ is shown in (C-2). In a 100 mL three-necked flask were placed 0.93 g (4.0 mmol) of <strong>[129013-83-8]3-(4-bromophenyl)pyridine</strong>, 1.3 g (4.0 mmol) of 4-(3-phenylquinoxalin-2-yl)phenylboronic acid, and 0.24 g (0.80 mmol) of tri(ortho-tolyl)phosphine. The atmosphere in the flask was replaced with nitrogen, and there were added 30 mL of ethylene glycol dimethyl ether (DME) and 4.0 mL of a 2.0 M aqueous potassium carbonate solution. The mixture was degassed by being stirred under reduced pressure, to which 14 mg (0.062 mmol) of palladium(II) acetate was added. The mixture was stirred under nitrogen stream at 80 C for 10 hours. After a predetermined time, water was added to the mixture, and an organic substance was extracted with chloroform from the aqueous layer. The extract was washed with a saturated aqueous sodium chloride solution together with the organic layer, and the organic layer was then dried over magnesium sulfate. The mixture was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and the filtrate was condensed to obtain a solid. The solid was purified by silica gel column chromatography (chloroform) and further recrystallized with chloroform/hexane; thus, 1.4 g of target white powder was obtained with a yield of 77 %. Then, 1.2 g of the obtained target substance was subjected to sublimation purification at 200 C under an argon stream (flow rate: 3.0 mL/min) and a pressure of 10 Pa for 19 hours; thus, 0.53 g of the target substance was obtained at a collection rate of 43 %. The compound was measured by nuclear magnetic resonance (NMR) spectrometry and identified as 2-phenyl-3-[4'-(3-pyridyl)biphenyl-4-yl]quinoxaline (abbr.: PPylPQ). The 1H NMR data is given as follows. 1H NMR (300 MHz, CDCl3): delta (ppm) = 7.37-7.41 (m, 4H), 7.57-7.81 (m,12H), 7.90-7.94 (m,1H), 8.18-8.21 (m, 2H), 8.61 (dd, J1 = 4.9 Hz, J2 = 1.5 Hz, 1H), 8.90 (d, J = 2.4 Hz, 1H). show 1H NMR charts. Note that shows an enlarged chart showing the range from 7.0 ppm to 9.0 ppm in |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | Reference Example 2: 5-(4-Bromophenyl-1-methyl)-1,2,3,6-tetrahydropyridine Iodomethane (0.5 ml, 8.0 mmol) was added to a solution of 199 mg (0.85 mmol) of <strong>[129013-83-8]3-(4-bromophenyl)pyridine</strong> in acetonitrile (11 ml), and the mixture was heated under reflux with stirring for 14 hr. The solvent was removed by distillation. The residue was dissolved in 2.7 ml of methanol and 2.7 ml of water. Sodium borohydride (292 mg) was added to the solution under ice cooling, and the mixture was stirred under ice cooling for one hr and at room temperature for 20 hr. The reaction solution was adjusted to pH 1 by the addition of 5 N hydrochloric acid and was then concentrated. The residue was adjusted to pH 9 by the addition of aqueous ammonia. The aqueous solution was extracted thrice with 10 ml of ethyl acetate. The organic layers were combined and were dried over anhydrous sodium sulfate followed by fitration. The filtrate was concentrated under the reduced pressure, and the residue was purified by column chromatography on silica gel (n-hexane: ethyl acetate = 1: 1 to chloroform: methanol = 20: 1) to give 126 mg (yield 59%) of the title compound. 1H-NMR (300 MHz, CDCl3) delta: 2.31-2.39 (2H, m), 2.44 (3H, s), 2.55 (2H, t, J = 6.0 Hz), 3.22-3.24 (2H, m), 6.08-6.12 (1H, m), 7.19 (2H, d, J = 8.4 Hz), 7.41 (2H, d, J = 8.4 Hz). MS (API) m/z: 252 (M++1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 644 teri-butyl 3-(4-bromophenyl)piperidine-l-carboxylateTo a solution of <strong>[129013-83-8]3-(4-bromophenyl)pyridine</strong> (0.4 g, 1.68 mmol) and HCl (1 .0 N solution in water, 1 .7 mL, 1 .7 mmol) in MeOH (20 mL) was added Pt02 (0.5 g) and stirred for 24 h at room temperature under H2 atmosphere (50 psi) in a Parr hydrogenation apparatus. The mixture was filtered through Celite, and the filtrate was evaporated under reduced pressure. The resulting white solid was dissolved in EtOAc (50 mL) and washed with 1 N NaOH ( 10 mL). The aqueous phase was extracted with EtOAc (3 x 50 mL), and the combined organic phase was dried(Na2S04). Evaporation of the solvent gave a white solid which was redissolved in DCM and added Boc20 followed by Et3N at 0 C. After stirring the reaction mixture for 1 h at room remperature diluted with DCM and washed sequentially with 1 N HCl, water and brine, dried over sodium sulfate, and evaporated under vacuum. Flash chromatography of the residue afforded the desired product as viscous mass (350 mg, 61 %) ESI MS m/z 341 [Ci6H22BrN02 + H]+. | ||
8.6 g | With hydrogenchloride; rhodium contaminated with carbon; hydrogen; In methanol; water; under 9120.61 Torr; for 24h;Autoclave; | Example 3 In an autoclave, Compound 2 (10.0g, 0.043mol) was added to 120mL of methanol, was added 11mL of hydrochloric acid, was added rhodium on carbon (0.80g, 5%) after introducing hydrogen reaction at 12 atm 24 hours after the completion of the reaction, the solid was filtered off, and methanol was mostly distilled off under reduced pressure and the filtrate was added 1mL of sodium hydroxide solution 130mL, 20 minutes of stirring, extracted twice (2 * 100mL) with ethyl acetate, the organic phase was washed with saturated citric acid 1 (100 mL), the organic phase was dried over anhydrous sodium sulfate, the organic phase is evaporated to give a pale yellow solid pressurized 8.6g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With caesium carbonate;copper(I) oxide; In N,N-dimethyl-formamide; at 140℃; for 72h;Inert atmosphere; | Synthetic example 6:1 , 1 ,-bis(4-(pyridin-3-yl)phenyl)-1 H,1 'H-2,2'-biimidazole6A mixture of 1H,1'H-2,2'-biimidazole (950 mg, 7.1 mmol), <strong>[129013-83-8]3-(4-bromophenyl)pyridine</strong> (4.95 g, 21.3 mmol) and Cs2C03 (9.24 g, 28.4 mmol) in DMF (80 mL) was degassed ( 2 bubbling, 15 min). Cu20 (410 mg, 2.9 mmol) was added and the mixture was heated (140 "C, 72h). The mixture was allowed to cool to room temperature and filtered through Celite washing with CH2CI2. The combined filtrate and washings were concentrated. The mixture was diluted with CH2CI2 and H20 and the organic phase was separated. The aqueous phase was re-extracted (CH2CI2) and the combined organics were washed (saturated aqueous NaCI), dried (MgS04), filtered and concentrated to give a solid residue. The residue was purified by flash chromatography (EtOAc/CH2CI2/MeOH 40:60:3 then 35:60:5 then 30:60:10) to give 1 ,1,-bis(4-(pyridin-3-yl)phenyl)-1 H,1'H-2,2'-biimidazole (1.05 g, 34%) as a colourless solid. A portion of this material was further purified firstly, by recrystallisation (CH2CI2/toluene/petrol) and then by distillation (sublimation apparatus 260 DC, 10"6 mBar): m.p. 218 - 223 C (DSC); 1H NMR (CDCI3, 400 MHz) delta 6.95 - 7.00 (m, 4H), 7.15 (d, J 1.2 Hz, 2H), 7.29 (d, J 1.2 Hz, 2H), 7.38 (ddd, J 0.6, 4.8, 7.9 Hz, 2H), 7.40 - 7.45 (m, 4H), 7.82 (ddd, J 0.6, 1.7, 7.9 Hz, 2H), 8.62 (dd, J 1.4, 4.8 Hz, 2H), 8.79 (d. J 1.9 Hz, 2H); 13C NMR (CDCI3, 100 MHz) delta 121.4, 123.7, 124.8, 127.7, 130.2, 134.1 , 135.2, 137.0, 137.2, 137.3, 148.1 , 149.0; HRMS (El) m/z 439.1665 CzeHig e [M - H]+' requires 439.1666. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With caesium carbonate;bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; for 12h;Inert atmosphere; Reflux; | In a stream of argon, 0.18 g (0.32 mmol) of 2-[3,5-bis(4,4,5,5-tetarmethyl-1,3,2-dioxabororan-2-yl)phenyl]-4,6-diphenylpyrimidine, 0.19 g (0.82 mmol) of 3-(4-bromophenyl)-pyridine, 0.25 g (0.76 mmol) of cesium carbonate and 23 mg (0.033 mmol) of dichlorobis(triphenylphosphine)palladium were suspended in 10 mL of tetrahydrofuran, and the obtained suspension was heated under reflux for 12 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 hexane/chloroform (1:1) mixed solvent as an eluent to give 77 mg of the target 2-[4,4"-di(3-pyridyl)-1,1' :3',1"-terphenyl-5'-yl]-4,6-diphenylpyrimidine as a white solid (yield: 39%). 1H-NMR(CDCl3):delta7.30-7.35(m,2H),7.39-7.50(m,6H),7.67(d,J=7.8 Hz,4H),7.84(d,J=7.8Hz,4H),7.86-7.93(m,2H),7.98(s,1H),8.22-8.24(m, 5H),8.55(d,J=4.3Hz,2H),8.88(bs,2H),8.91(bs,2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: A microwave vial is charged with INTERMEDIATE J (1 eq.), the appropriate aryl bromide (1 eq.), Siliacat-DPP-Pd (0.26 mmol/g, 0.1 eq.), Cs2C03 (2.2 eq.) and acetonitrile. The mixture is heated in the micro waved for 30 minutes at 100C, filtered on Celite and concentrated to dryness. The residue is dissolved in MeOH, treated with 0.5 M NaOMe (0.5 eq.) and stirred overnight at room temperature. AcOH (0.5 eq.) is then added and the mixture is concentrated to dryness and purified by reverse phase preparative HPLC to give the desired product. Table 5 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; palladium; In toluene; at 80℃; for 16h;Inert atmosphere; | Under N2 gas purification system, Compound A, 0.9 equivalents of compound B, 0.05 equivalents of Pd (0) and 4.0 equivalents of potassium carbonate into toluene, and the mixture was stirred in an oil bath at 80 deg. C. After 16 hours, water was added to the mixture, was extracted and the resultant with hexane and ethylene glycol diacetate (8: 2) developing solvent through the column to obtain a white solid compound C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With bis-triphenylphosphine-palladium(II) chloride; potassium acetate; In 1,4-dioxane; for 5h;Inert atmosphere; Reflux; | In a flask,Intermediate 2-4 (13g, 56mmol),United pinacolato ester (21.3g, 84mmol),Potassium acetate (20g, 200mmol),Dioxane (300ml) and bistriphenylphosphine palladium dichloride (1g),Under nitrogen was heated to reflux for 5 hours.cool down,concentrate,The crude product was purified by column chromatography to give the product 14.6g,Yield 93%. |
15.0 g | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; for 4h;Inert atmosphere; Reflux; | <strong>[129013-83-8]3-(4-bromophenyl)pyridine</strong> 14.0g, bis(pinacolato)diboron 18.3g, 1,1'-bis(diphenylphosphino)ferrocenedichloropalladium(II) dichloromethane complex 1.5g, potassium acetate 11.8g, cyclopentylmethyl ether(CPME) 100 ml in a flask, under nitrogen atmosphere this mixture was stirred for 4 hours at reflux temperature. The liquid water addition, toluene liquid to room temperature by cooling the reaction. The organic layer is concentrated, activated carbon dissolved in toluene at column chromatography is purified (soln.: toluene), 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine (15.0g) is obtained. |
Tags: 129013-83-8 synthesis path| 129013-83-8 SDS| 129013-83-8 COA| 129013-83-8 purity| 129013-83-8 application| 129013-83-8 NMR| 129013-83-8 COA| 129013-83-8 structure
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