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Product Citations

Stephen H. Dempsey ; Alex Lovstedt ; Steven R. Kass ;

Abstract: A variety of electrostatically enhanced 3- and 4-pyridylborate salt catalysts are reported and show significant improvement over an activated noncharged neutral control compound. Their nucleophilicity in a stoichiometric SN2 reaction and catalytic performance in a urethane synthesis are evaluated along with three methods for rapidly evaluating the basicity of these species. That is, qualitative titrations in CH2Cl2 and CHCl3 were carried out, two separate solution-state IR studies in CCl4 and CDCl3 are reported, and the proton affinities of the anionic components of the salts were computed. Charge differences between the anion and its protonated zwitterionic conjugate acid are evaluated along with the highest occupied molecular orbitals of the anions in relationship to some of the surprising reactivity findings that were observed in the two kinetic studies.

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Product Details of Pyridin-3-ylboronic acid

CAS No. :1692-25-7
Formula : C5H6BNO2
M.W : 122.92
SMILES Code : OB(C1=CC=CN=C1)O
MDL No. :MFCD00674177
InChI Key :ABMYEXAYWZJVOV-UHFFFAOYSA-N
Pubchem ID :2734378

Safety of Pyridin-3-ylboronic acid

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

Application In Synthesis of Pyridin-3-ylboronic acid

* 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 [ 1692-25-7 ]

[ 1692-25-7 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 13195-50-1 ]
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  • [ 2302-25-2 ]
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  • [ 51746-85-1 ]
  • 3
  • [ 7051-15-2 ]
  • [ 1692-25-7 ]
  • [ 334977-38-7 ]
  • 4
  • [ 66996-59-6 ]
  • [ 1692-25-7 ]
  • [ 869120-20-7 ]
  • C21H16N2O [ No CAS ]
  • 5
  • [ 7149-14-6 ]
  • [ 1692-25-7 ]
  • 3-(2'-bromo-4'-nitrophenyl)pyridine [ No CAS ]
  • 6
  • [ 83279-39-4 ]
  • [ 1692-25-7 ]
  • [ 628710-83-8 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100.0℃; for 40.0h;Nitrogen atmosphere; A solution of <strong>[83279-39-4]3-chloro-4-trifluoromethoxybenzaldehyde</strong> (3 g, 13.3 mmol) and 3- pyridylboronic acid (1.97 g, 16.0 mmol) in dioxane (70 [ML)] and 2M [K2CO3] (20 mL) is degassed with nitrogen prior to addition of Pd (PPh3) 4 (1.5 g, 1.33 mmol). The mixture was stirred at [100C] under nitrogen for 40 hours, then cooled and filtered on celite/silica and the filtrate concentrated under reduced pressure. The crude was purified by column chromatography (2/1 heptane/ethyl acetate) to give 1.51 g of title compound. [C13H8F3NO2] Mass (calculated): [267]; (found) [[M+H+]] = 268 NMR (400 MHz, [CDCL3] : 7.3-7. 35 [(1H,] m, aryl-H); 7.4-7. 45 [(1H,] m, aryl-H); 7.7-7. 75 [(1H,] m, aryl- H); 7.9-8 (2H, n, aryl-H); 8.65 [(1H,] bs, aryl-H); 8.7 [(1H,] bs, aryl-H).
  • 7
  • [ 3934-20-1 ]
  • [ 1692-25-7 ]
  • [ 483324-01-2 ]
YieldReaction ConditionsOperation in experiment
74.6% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 90℃; for 4h;Inert atmosphere; Green chemistry; In a 250 mL three-necked flask,2,4-dichloropyrimidine (5.0 g, 33.56 mmol)Dissolved in 1,4-dioxaneAnd water (4: 1, 50 mL) A solution of 3-boronic acid pyridine (4.95 g, 40.27 mmol),Potassium carbonate (9.28 g, 67.12 mmol)And Pd (dppf) Cl2 (2.45 g, 3.36 mmol);The system was replaced with argon three times,Gradually heated to 90 C,Reaction for 4 hours;After the reaction, the system was concentrated under reduced pressure to remove most of the solvent,Ethyl acetate (150 mL)And water (100 mL),Extraction and separation,The aqueous phase was then extracted with ethyl acetate (80 mL)The organic phases were combined,Re-water (80 mL x 2) and saturateWashed with brine (80 mL x 2)Liquid separation,The organic phase was dried over anhydrous sodium sulfate for 3 hours,Filtration and concentration,Crude;The crude product was added petroleum ether (32 mL)And ethyl acetate (6 mL) were stirred for 1 hour,filter,Dried in vacuo to give 4.8 g of 2-chloro-4- (3-pyridyl) pyrimidine,The yield was 74.6%Purity HPLC was greater than 95%.
73% With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; water; for 16h;Heating; Reflux; Inert atmosphere; Example 11 Preparation of 2-chloro-4-(pyridin-3-yl)pyrimidine[00106] Into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen were placed a solution of pyridin-3-ylboronic acid (4.42 g, 36.0 mmol, 1.00 equiv) in THF/H2O (30 mL), a solution of 2,4-dichloropyrimidine (5.40 g, 36.2 mmol, 1.00 equiv) in THF/H2O (30 mL), Na2CO3 (11.5 g, 108 mmol, 3.00 equiv) and PdCl2(PPh3)2 (1.80 g, 2.57 mmol, 0.06 equiv). The resulting solution was heated to reflux for 16 hrs in an oil bath. The reaction mixture was cooled and quenched by the addition of 100 mL of water. The resulting solution was extracted with 5x200 mL of ethyl acetate. The organic layers were combined, washed with 3x200 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1: 1). This resulted in 5 g (73%) of 2-chloro-4-(pyridin-3-yl)pyrimidine as a yellow solid.
52% With bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; for 14h;Reflux; Inert atmosphere; General procedure: To a solution of 2,4-dichloro-5-methylpyrimidine (500 mg, 3.1 mmol) and 4-trifluoromethoxylphenylboronic acid (644 mg, 3.1 mmol) in dioxane (15 mL), Pd(PPh3)2Cl2 (215 mg, 0.3 mmol) and 2M Na2CO3 (920 mg, 8.7 mmol) were added. The mixture was stirred at reflux for 14 h under N2 atmosphere. The reaction mixture was cooled to room temperature and filtrated. The filtrate was diluted with H2O (100 mL) and then extracted with EtOAc, and the organic layer was dried over anhydrous Na2SO4, After filtration, the filtrate was evaporation and purified by chromatography (petroleum ether/ EtOAc, 5:1) to give the product as oil (700 mg, 73 %).
With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; water; at 60℃; for 16h; Step 1.Synthesis of 2-chloro-4-(3-pyridyl)pyrimidine nitrogen was bubbled through a solution of 2,4-dichloropyrimidine (1 eq) in tetrahydrofuran and water (3:1) for 0.5 h. bis(diphenylphosphino)ferrocene Palladium(II)chloride (0.05 eq) followed by pyridine-3-boronic acid (1 eq) and sodium carbonate (3 eq) was added and the mixture was heated to 60 C. for 16 h under nitrogen.The reaction mixture was concentrated and partitioned between ethyl acetate and water.The organic layer was washed with brine and dried with sodium sulfate and concentrated.Purification on silica gel gave 2-chloro-4-(3-pyridyl)pyrimidine. MS: MH+=190.
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; potassium carbonate; In 1,2-dimethoxyethane; water; at 100℃; for 1h; 2-Chloro-4-(pyridin-3-yl)pyrimidine: Pyridin-3-ylboronic acid (263 mg, 2.14 mmol), PEPPSI - IPr (132 mg, 0.195 mmol), and potassium carbonate (2.4 ml of 2 M aqueous solution, 4.8 mmol) were added to 2,4-dichloropyrimidine (290 mg, 1 .95 mmol) in 1 ,2- dimethoxyethane (8 mL) . The reaction mixture was stirred at 100 C for 1 h. The solvents were removed under reduced pressure, and the residue was dissolved in DCM and filtered. The filtrate was purified with silica gel chromatography (20% - 60% EtOAc in hexanes) to yield 150 mg, 40.2 % yield of the title compound. 1H NMR (400 MHz, CHLOROFORM-d) delta 1 H NMR (400 MHz, CHLOROFORM-d) delta 9.28 (br. s., 1 H), 8.79 (d, J = 3.92 Hz, 1 H), 8.73 (d, J = 5.09 Hz, 1 H), 8.46 (d, J = 8.03 Hz, 1 H), 7.72 (d, J = 5.29 Hz, 1 H), 7.49 (dd, 1 H). LCMS: tR = 0.47 min, 93%. MS m/z = 192 (M+H)+.

  • 8
  • [ 1692-25-7 ]
  • [ 33332-28-4 ]
  • [ 925677-98-1 ]
YieldReaction ConditionsOperation in experiment
86% With caesium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 90℃; for 16h; 6-Pyridin-3-ylpyrazin-2-amine An oven dried resealable Schlenk tube was charged with 6-chloropyrazin-2-amine (0.73 g, 5.71 mmol), 3-pyridineboronic acid (0.91 g, 7.42 mmol), dioxane (50 mL) and a 2M aqueous solution of cesium carbonate (8.5 mL, 17.13 mmol). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and 1 ,1'- bis(diphenylphosphino)ferrocene-palladium(ll) dichloride dichloromethane complex (290mg, 0.35 mmol) was added. After three new cycles of evacuation-backfilling with argon, the Schlenk tube was capped and placed in a 9O0C oil bath. After 16h, the mixture was cooled, partitioned between water and ethyl acetate, the aqueous phase extracted twice with ethyl acetate, the organic layers washed with brine, dried (MgSO4) and evaporated. The residue was purified by silica gel flash chromatography (95:5 dichloromethane/methanol) to give the title compound (845 mg, 86percent) as a solid. delta 1H-NMR (CDCI3): 9.18 (s, 1H), 8.67 (d, 1H), 8.38 (s, 1H), 8.25 (m, 1H), 7.99 (s, 1 H), 7.41 (m, 1 H), 4.77 (s, 2H). ESI/MS (m/e, percent): 172 [(M+1)\\ C9H8N4].
  • 9
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  • [ 1692-25-7 ]
  • [ 869120-20-7 ]
  • 10
  • [ 808744-34-5 ]
  • [ 1692-25-7 ]
  • [ 1067914-66-2 ]
YieldReaction ConditionsOperation in experiment
75% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; acetonitrile; at 60℃; for 18h; Step B: Preparation of 7-(pyridin-3-yl)imidazori.2-a1pyridine:; A suspension of potassium carbonate (0351 g, 2.54 mmol), pyridin-3-ylboronic acid (68.6 mg5 0.558 mmol), 7- bromoimidazo[l52-a]pyridine (0.100 g, 0.508 mmol) and tetrakis(triphenylphosphine) <n="70"/>palladium (0) (29.3 mg, 0.025 mmol) in 6.5 ml of a 1:1 :4.5 mixture of water:dimethylformamide:acetonitrile was degassed thoroughly under a nitrogen atmosphere, and heated at 60 0C for 18 hours. The reaction mixture was poured in water (50 ml) and extracted with dichloromethane and EtOAc. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated to afford a solid. The solid was purified by silica gel chromatography (eluting with 6% MeOH-chloroform) to afford the desired compound (74.1 mg, 75 % yield). MS APCI (+) m/z 196.3 (M+l) detected.
75% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; acetonitrile; at 60℃; for 18h; A suspension of potassium carbonate (0.351 g, 2.54 mmol), pyridine-3-ylboronic acid (68.6 mg, 0.558 mmol), 7-bromoimidazo[l,2-a] pyridine (0.100 g, 0.508 mmol) and tetrakis(triphenylphosphine) palladium (0) (29.3 mg, 0.025 mmol) in 6.5 ml of a 1:1 :4.5 mixture of water:dimethylformamide:acetonitrile was degassed thoroughly under a nitrogen atmosphere, and heated at 60 C for 18 hours. The reaction mixture was poured in water (50 ml) and extracted with dichloromethane and EtOAc. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated to afford a solid. The solid was purified by silica gel chromatography (eluting with 6% MeOH-chloroform) to afford the desired compound (74.1 mg, 75 % yield). MS APCI (+) m/z 196.3 (M+l) detected.
  • 11
  • [ 1692-25-7 ]
  • [ 121554-10-7 ]
  • [ 934470-17-4 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 100℃; for 72h; Reference Example 11 5-Bromo-2-iodobenzonitrile and 3-pyridylboric acid were dissolved in a mixture solution of aqueous 2 M sodium carbonate solution and toluene, then tetrakis(triphenylphosphine)palladium was added thereto, and the mixture was heated, stirred with heating in an argon atmosphere at 100C for 3 days to obtain 5-bromo-2-pyridin-3-ylbenzonitrile. EI: 258, 260.
  • 12
  • [ 589-87-7 ]
  • [ 1692-25-7 ]
  • [ 129013-83-8 ]
YieldReaction ConditionsOperation 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 %.
  • 13
  • [ 474706-74-6 ]
  • [ 1692-25-7 ]
  • [ 1276109-83-1 ]
  • 14
  • [ 13534-90-2 ]
  • [ 1692-25-7 ]
  • [ 1356406-39-7 ]
  • 15
  • [ 1692-25-7 ]
  • [ 19733-56-3 ]
  • 16
  • [ 51376-06-8 ]
  • [ 1692-25-7 ]
  • [ 1395071-75-6 ]
  • 17
  • [ 3993-78-0 ]
  • [ 1692-25-7 ]
  • [ 66521-66-2 ]
YieldReaction ConditionsOperation in experiment
72% With 1-(2,6-diisopropylphenyl)-3-(2-oxo-2-(2,4,6-tri-tert-butylphenylamino)ethyl)-1H-imidazol-3-ium bromide; palladium diacetate; sodium hydroxide; In water; dimethyl sulfoxide; at 100℃; for 10h;          Pd(OAc)2  (35.00 mg, 0.15 mmol) and 1-(2,6-diisopropylphenyl)-3-(2-oxo-2-(2,4,6-tri-tert-butylphenylamino)ethyl)-1H-imidazol-3-iumbromide (96.00 mg, 0.15 mmol) was dissolved in 10 ml of DMSO : H2O,and 4-chloropyrimidin-2-amine (2.00 g, 15.43 mmol), NaOH (0.93 g, 23.15 mmol),pyridin-3-ylboronic acid (2.28 g, 18.5 mmol)  were added. The mixture was heated to 100 oCand stirred for 10h. After cooling, the mixturewas poured into EtOAc (40.0 mL and washed with water (2 ×10.0 mL), brine (2 × 25.0 mL), then dried over MgSO4, evaporation ofthe solvent under reduced pressure provided the crude product, which waspurified by column chromatography (hexane : EtOAc = 1:1) afford product as off white solid 1.92 g, 11.15 mmol) in 72percent yield. 1HNMR (300 MHz, DMSO): delta 9.23(dd, J =1.5 Hz, 1H), 8.68 (dd, J1= 3.0 Hz, J2 = 1.8 Hz,1H), 8.41-8.35 (m, 2H), 7.55-7.50 (m, 1H), 7.20 (d, J1 = 5.1 Hz, 1H), 6.78 (bs, 2H);   13C NMR (75 MHz, CDCl3): delta 163.8, 161.6, 159.4, 151.1, 148.0, 134.1,123.7, 106.0. HRMS(ESI) calcd. for C9H9N4 [M+H]+173.0827, found 173.0825.
  • 18
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  • [ 85333-43-3 ]
  • [ 1334167-24-6 ]
  • 20
  • [ 71759-89-2 ]
  • [ 1692-25-7 ]
  • [ 51746-85-1 ]
YieldReaction ConditionsOperation in experiment
52% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; N,N-dimethyl-formamide; at 110℃; for 2h;Microwave irradiation; Inert atmosphere; General procedure: Method B: In a20 mL microwave Biotage tube, a 1M Na2CO3 aqueous solution(5 mL) purged with argon were introduced into a mixture purged with argon of 4-iodo-1H-imidazole (1a) (0.194 g, 1.0 mmol), a boronicacid 2 (1.6 mmol) and Pd(PPh3)4 (0.80 g, 0.05 mmol) in DMF (15 mL). The mixture washeated under microwaveirradiation. When the reaction was complete, the mixture was cooled toroom temperature and concentrated under reduced pressure. The residue waspurified by flash chromatography on silica gel to provide compounds 3j and 3p-3u in yields ranging from 30 to 95%. Time and temperaturereactions were collected in Table 1.
  • 21
  • [ 106-37-6 ]
  • [ 1692-25-7 ]
  • [ 129013-83-8 ]
YieldReaction ConditionsOperation 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.
  • 22
  • [ 1813-33-8 ]
  • [ 1692-25-7 ]
  • [ 935520-50-6 ]
YieldReaction ConditionsOperation in experiment
With 1,1'-bis-(diphenylphosphino)ferrocene; tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; toluene; for 12h;Reflux; General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol), appropriate boronic acid (1.20 mmol)were dissolved in toluene/dioxane:2 N Na2CO3 (2:1:1) solution(6 ml). Tetrakis(triphenyl-phosphine)palladium(0) (0.10 mmol)and 1,10-Ferrocenediyl-bis(diphenylphosphine) (0.20 mmol) wasadded to the mixture and it was refluxed for 12 h. After cooleddown to ambient temperature, the reaction was filtered over celiteand extracted with EtOAc twice. The combined organic extractswere dried over MgSO4, filtered, and concentrated in vacuo. Theresidue was purified by flash column chromatography on silicagel using EtOAc/hexanes (1:10) eluant condition. (R-B(OH)2 =1-pentenyl boronic acid for 53, 1-cyclohexenylboronicacid for 54).
  • 23
  • [ 442127-50-6 ]
  • [ 1692-25-7 ]
  • 6-chloro-3,3'-bipyridin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 80℃; for 16.0h;Inert atmosphere; To a solution of 3-bromo-6- chloropyridin-2-amine (1 g, 4.82 mmol) in 1,4-dioxane (40 mL) and water (4 mL) were added pyridin-3-ylboronic acid (0.65 g, 5.30 mmol), potassium carbonate (1.33 g, 9.64 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.56 g, 0.48 mmol). The resulting solution was stirred for 16 hours at 80 C under nitrogen atmosphere. After cooling down to ambient temperature, the resulting mixture was diluted with water (100 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic layers was washed with brine (30 mL) and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography, eluted with 1-2% methanol in dichloromethane to afford 6-chloro-3,3'-bipyridin-2-amine as a light yellow solid: MS (ESI, m/z): 206.1 [M + 1]+; 1H NMR (400 MHz, OMSO-d6) delta 8.66 (s, 1H), 8.57 (dd, J= 2.0 Hz, 4.4 Hz, 1H), 7.84-7.82 (m, 1H), 7.48-7.45 (m, 1H), 7.38 (d, J= 7.6 Hz, 1H), 6.69 (d, J= 11.6 Hz, 1H), 6.28 (br s, 2H).
  • 24
  • [ 166402-16-0 ]
  • [ 1692-25-7 ]
  • 3-(pyridin-3-yl)quinoxalin-6-amine [ No CAS ]
  • 25
  • [ 1246765-38-7 ]
  • [ 1692-25-7 ]
  • 6-(pyridin-3-yl)-3,4-dihydroquinazolin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water;Inert atmosphere; Reflux; General procedure: Heteroarylboronic acid (1.3 equivalents), aryl bromide (1 equivalent), and tetrakis(triphenylphosphine) palladium(0) (5mol %) were suspended in DME to give a 0.07-0.1M solution of boronic acid under nitrogen atmosphere. A 0.5M aqueous solution of sodium carbonate (6 equivalents) was added. The mixture was refluxed for 3.5-14h, cooled to room temperature, diluted with water and extracted several times with ethyl acetate. The combined extracts were dried over anhydrous MgSO4, concentrated and purified by flash chromatography and were if necessary recrystallized.
  • 26
  • [ 1196155-38-0 ]
  • [ 1692-25-7 ]
  • 6-(trifluoromethyl)-[2,3'-bipyridine]-4-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In water; acetonitrile; A mixture of <strong>[1196155-38-0]2-chloro-6-(trifluoromethyl)isonicotinonitrile</strong> 1 (125 mg, 0.605 mmol), 3- pyridylboronic acid (90 mg, 0.738 mmol), 2M aq. Na2C03 solution (0.6 mL), and ACN (3 mL) was purged with nitrogen at RT for 3 min. [l, l '-Bis(diphenylphosphino)ferrocene] dichloropalladium(II) complex with DCM (1 : 1) (5 molpercent) was added, and the mixture heated at 100 °C for 4 h. The mixture was concentrated and purified via silica gel chromatography to afford compound 2 (114 mg, 76percent) a as white solid. LCMS Mass: 250 (M++l).
  • 27
  • [ 82632-80-2 ]
  • [ 1692-25-7 ]
  • [ 1427002-41-2 ]
YieldReaction ConditionsOperation in experiment
26% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; for 28h;Inert atmosphere; Reflux; Obtained 2,3,6,7,10,11-hexa-bromo triphenylene 3.46g, and 3-pyridine boronic acid 4.0g, 2Maqueous solution of potassium carbonate 22.4ml, tetrakis (triphenylphosphine) palladium (0)0.57 g, toluene 180 ml, of ethanol 45ml and heated in addition to the reaction vessel wasreplaced with nitrogen, it was refluxed with stirring for 28 hours. After cooling to roomtemperature and added water 100 ml, chloroform 500 ml, was collected and the organic layer byperforming a liquid separation operation. The organic layer was washed with water 100 ml, driedover anhydrous magnesium sulfate to give the crude product by concentration. The resultingcrude product was purified by performing recrystallization from 1,2-dichlorobenzene,2,3,6,7,10,11 class of hexa (pyridin-3-yl) triphenylene (Compound 2) White obtained powder0.9g (26% yield).
  • 28
  • [ 32138-69-5 ]
  • [ 1692-25-7 ]
  • [ 154229-19-3 ]
YieldReaction ConditionsOperation in experiment
71.8% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In water; N,N-dimethyl-formamide; at 75 - 80℃; for 36h; 10 g of compound VIII was added, and 300 ml of N, N-dimethylformamide was dissolved, and 3 g of 3-pyridineboronic acid was added, and 90 mg of bis (triphenylphosphine) palladium dichloride, 50 ml of water, 10.5 g of sodium carbonate ~ 80 reaction for 36 hours; cooling, filtration; filtrate water 600ml stirring crystallization, filtration, the compound IX crude; HPLC purity: 82.6%, which contains impurities X1.9%.The crude product was stirred at about 65 C for 1 hour, cooled and filtered. The filter cake was dried under reduced pressure at about 50 C to give 6.3 g of Compound IX; HPLC purity: 98.3%, containing impurities X0.9 %; Yield: 71.8%.
With palladium on activated charcoal; sodium carbonate; In dimethyl sulfoxide; at 120℃; for 12h; In 1000 ml of the magneton with stirring, of the reflux condensation tube of three compound is added in the flask 17 - iodine male steroid - 5, 16 - diene - 3 beta - hydroxy 39.8 g (0.10 muM, 1.0 equiv), pyridine -3 - boric acid 24.6 g (0.20 muM, 2.0 equiv), palladium/carbon (to palladium) 1.06 g (0.01 muM, 0.1 equiv), adding sodium carbonate 21.2 g (0.20 muM, 2.0 equiv), adding dimethyl sulfoxide 500 ml as the solvent, nitrogen replacement heating to 120 C reaction 12 hours. After the reaction, distilled under reduced pressure (the distillation temperature is 50 C, vacuum degree is -0.08 mpa) to remove the solvent, by adding dichloromethane 500 ml and triethylamine 11.1 g (0.11 muM, 1.1 equiv) solution, adding 4 - dimethyl aminopyridine 0.62 g (0.005 muM, 0 . 05 equiv) as catalyst, lowering the temperature to 0 C, slowly dropping vinegar anhydride 15.3 g (0.15 muM, 1.5 equiv), the end of the [...], raising the temperature to 25 C after three hours to continue the reaction after the palladium/carbon catalyst filter recovery, organic layer is 500 ml water, 500 ml 1 N sodium bicarbonate solution and then concentrated under reduced pressure (the distillation temperature is 30 C, vacuum degree is -0.07 mpa) to dry, adding 120 g acetone heating [...] after two hours the temperature slowly to 0 C to crystallize, get acetate 26.1 g, purity of 98.8%, two-step molar yield of 66.0%, by HPLC and conclusive evidence of the NMR detection is acetate.
  • 29
  • [ 53848-17-2 ]
  • [ 1692-25-7 ]
  • N-(2-methyl-6-(pyridine-3-yl)phenyl)-2-phenylacetamide [ No CAS ]
  • 30
  • [ 53848-17-2 ]
  • [ 1692-25-7 ]
  • C12H12N2 [ No CAS ]
  • 31
  • [ 808744-34-5 ]
  • [ 1692-25-7 ]
  • [ 1067914-67-3 ]
  • 32
  • [ 1001070-33-2 ]
  • [ 1692-25-7 ]
  • 1-(phenylsulfonyl)-5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]
  • 33
  • [ 19063-56-0 ]
  • [ 1692-25-7 ]
  • 7-(pyridin-3-yl)-2H-chromen-2-one [ No CAS ]
  • 34
  • [ 1692-25-7 ]
  • [ 4385-77-7 ]
  • 35
  • [ 4805-22-5 ]
  • [ 1692-25-7 ]
  • 3-(5′-bromo-[2,2′-bisthiophene]-5-yl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 80℃; for 48h;Inert atmosphere; Take 5,5′-dibromo-2,2′-bisthiophene (0.325g 1.0mmol), 3-pyridineboronic acid (0.246g 2.0mmol),Tetrakis (triphenylphosphine) palladium (0.035g 0.03mmol) and potassium carbonate (1.106g 8.0mmol) were mixed in a 100mL reaction device,After the reaction device was evacuated, nitrogen was passed through it, and the operation was repeated three times. Then, a mixture of 18 mL of toluene, 9 mL of ethanol, and 3 mL of water was added, and the mixture was refluxed at 80 C for 2 days under the protection of nitrogen.After the reaction was completed, the layers were cooled and separated, extracted with dichloromethane, the organic phases were combined, washed with saturated brine and dried over magnesium sulfate to remove water.The solvent was removed with a rotary evaporator to obtain a solid powder, which was then separated through a column with an eluent of petroleum ether: ethyl acetate = 1: 1 (volume ratio) to obtain a pale yellow solid powder.
 

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