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CAS No. : | 63279-58-3 | MDL No. : | MFCD01166242 |
Formula : | C10H6BrI | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HQHHKYXPFKHLBF-UHFFFAOYSA-N |
M.W : | 332.96 | Pubchem ID : | 5073667 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 64.37 |
TPSA : | 0.0 Ų |
GI absorption : | Low |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.13 cm/s |
Log Po/w (iLOGP) : | 2.68 |
Log Po/w (XLOGP3) : | 4.51 |
Log Po/w (WLOGP) : | 4.21 |
Log Po/w (MLOGP) : | 4.86 |
Log Po/w (SILICOS-IT) : | 4.61 |
Consensus Log Po/w : | 4.17 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -5.36 |
Solubility : | 0.00145 mg/ml ; 0.00000434 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.23 |
Solubility : | 0.0196 mg/ml ; 0.0000587 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.85 |
Solubility : | 0.000475 mg/ml ; 0.00000143 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.41 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
85% | With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 20℃; for 3 h; Inert atmosphere | 1-amino-4bromonaphthalene (60g 027mo1) was added to the one-neck flask and an argon atmosphere was established in a vacuum. After adding acetonitrile (500m]), the mixture was stored at 0C until 1-amino-46iromonaphthalene is dissolved. tBurylnitrite (42g, 49m1, 0.41mo1), and copper bromide (73g, 0.32mol) was stirred at room tempwnamre fmr3 hours. Upon completion of the reaction, 1 N HCI aqueous solution (600ml) was added and stored. After filtering a produced solid, the obtained solid was washed with distilled water and ether. Pare Compound L (76g, 85percent) was obtained by column chromatography. |
83% | Stage #1: With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5 h; Inert atmosphere Stage #2: With potassium iodide In water at 0℃; Inert atmosphere |
Example I-IVPreparation of Compound 307General Procedure I-ZTo a stirred solution of 4-bromonaphthalen-1-amine (I-IVa) (5.00 g, 22.52 mmol) in 60 mL of concentration HCl was added NaNO2 (3.10 g, 44.92 mmol) in 10 mL of H2O at 0° C. under argon. After addition, the solution was stirred for 0.5 hour, then potassium iodide (KI) was added (7.43 g, 44.92 mmol) in 10 mL of H2O at 0° C. under argon, stirring was continued overnight. The solution was diluted with 100 mL AcOEt, followed by 100 mL H2O. The aqueous layer was separated and extracted by EtOAc (100 mL.x.3). The organic layers were combined and washed with the brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel to afford 1-bromo-4-iodonaphthalene (I-IVb) (6 g, yield 83percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 20℃; for 3h;Inert atmosphere; | 1-amino-4bromonaphthalene (60g 027mo1) was added to the one-neck flask and an argon atmosphere was established in a vacuum. After adding acetonitrile (500m]), the mixture was stored at 0C until 1-amino-46iromonaphthalene is dissolved. tBurylnitrite (42g, 49m1, 0.41mo1), and copper bromide (73g, 0.32mol) was stirred at room tempwnamre fmr3 hours. Upon completion of the reaction, 1 N HCI aqueous solution (600ml) was added and stored. After filtering a produced solid, the obtained solid was washed with distilled water and ether. Pare Compound L (76g, 85percent) was obtained by column chromatography. |
83% | Example I-IVPreparation of Compound 307General Procedure I-ZTo a stirred solution of 4-bromonaphthalen-1-amine (I-IVa) (5.00 g, 22.52 mmol) in 60 mL of concentration HCl was added NaNO2 (3.10 g, 44.92 mmol) in 10 mL of H2O at 0° C. under argon. After addition, the solution was stirred for 0.5 hour, then potassium iodide (KI) was added (7.43 g, 44.92 mmol) in 10 mL of H2O at 0° C. under argon, stirring was continued overnight. The solution was diluted with 100 mL AcOEt, followed by 100 mL H2O. The aqueous layer was separated and extracted by EtOAc (100 mL.x.3). The organic layers were combined and washed with the brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel to afford 1-bromo-4-iodonaphthalene (I-IVb) (6 g, yield 83percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; for 7h;Heating / reflux; | Synthesis Example 1 (Synthesis of a compound (AN-1)); Under the atmosphere of argon, 10 g of <strong>[63279-58-3]1-bromo-4-iodonaphthalene</strong> and 6 g of 4-bromophenylboronic acid which were synthesized in accordance with conventional processes were dissolved into 150 ml of toluene, and 45 ml of a 2M aqueous solution of sodium carbonate was added. Then, 1 g of tetrakistriphenylphosphinepalladium was added, and the resultant mixture was heated under the refluxing condition for 7 hours. After one night, the formed organic layer was extracted with toluene, washed with water and a saturated aqueous solution of sodium chloride. The organic layer was dried with anhydrous sodium sulfate, and the solvent was removed by distillation. The residue was purified in accordance with the silica gel column chromatography (the solvent of development: toluene/hexane), and 6.3 g of 1-bromo-4-(4-bromophenyl)-naphthalene was obtained (the yield: 58percent). The obtained 1-bromo-4-(4-bromophenyl)naphthalene in an amount of 6 g was mixed with 10 g of 10-phenylathracene-9-boronic acid synthesized in accordance with a conventional process and 150 ml of DME. Then, 1.1 g of tetrakistriphenylphosphinepalladium and 50 ml of a 2M aqueous solution of sodium carbonate were added, and the atmosphere was purged with argon. After the resultant mixture was heated under the refluxing condition for 7.5 hours, the mixture was cooled by leaving standing, and formed crystals were separated by filtration. The separated crystals were washed with water, methanol and then heated toluene, and 8.3 g of the object compound (AN-1) was obtained as a light yellow solid substance (the yield: 70percent). When the obtained compound was examined in accordance with the field desorption mass spectroscopy (FDMS), it was found that m/z=708, which agreed with C56H36=708, and the above compound was identified to be Compound AN-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; for 2.5h;Inert atmosphere; Reflux; | (1) Synthesis of BrCl Raw Material[00147 ][Chem. 22][00148] Reagents and solvents described below were charged into a 300-mL recovery flask.l-Bromo-4-iodonaphthalene : 5.00 g (15.0 mmol)4-Chloro-2-formylphenylboronic acid: 2.64 g (14.3 mmol) Tetrakis (triphenylphosphine) palladium ( 0 ) : 0.50 g (0.43 mmol) Toluene: 100 mLEthanol: 50 mL Aqueous solution of 10percent by weight sodium carbonate: 50 mL[00149] The resulting reaction mixture was heated to reflux for 2.5 hours with stirring under nitrogen. After the completion of the reaction, the reaction solution was washed with water, dried over sodium sulfate, and concentrated to give a crude product. The crude product was then purified by silica gel column chromatography (eluent:heptane/chloroform = 3/1) to give 3.90 g (yield: 79percent) of oily l-bromo-4- ( 4-chloro-2-formylphenyl ) naphthalene . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; water;Inert atmosphere; Reflux; | General Procedure I-AAThe mixture of <strong>[63279-58-3]1-bromo-4-iodonaphthalene</strong> (I-IVb) (6.00 g, 18.01 mmol), 4-methoxyphenylboronic acid (2.74 g, 18.01 mmol), Na2CO3 (3.82 g, 36.02 mmol) and Pd(dppf)Cl2 (658 mg, 0.90 mmol) in 50 mL of THF and 10 mL of H2O was heated to reflux under argon overnight. The mixture was concentrated, the residue was partitioned between H2O and DCM, the aqueous phase was extracted with DCM. The combined organic layer was washed with brine, dried over Na2SO4, and concentrated. The residue was purified by chromatography on silica gel to afford 1-bromo-4-(4-methoxyphenyl)naphthalene (I-IVd) (4.50 g, yield 63percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With 18-crown-6 ether; potassium carbonate;copper; In 1,2-dichloro-benzene; at 180℃; for 6h;Inert atmosphere; | Compound L (40g, 0.12mo1), carbamte (24.18 0.14mop, capper (3.3g, O.OSmop, 18-crown-6 (2.3g, 0.009mop, and K,_CQ, (66.38 0.48mo1) were added to the two-neck flask and an argon atmosphere was established in a vacuum. 7,2-dichloroben7ene (250mp was added and the mixture was stirred under reflex at 180C for 6 hours. Upon completion of the reaction, copper was removed by using Celite filter and the reaction mixture was dissolved with MC. After removing a solvent. Pure Compound M (36g, (81 %) was separated by column chromatography using dichtoromethane and hexane as an eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
copper(I) iodide; In n-heptane; water; triethylamine; | Synthesis Example 21-Bromo-4-(4-n-propylphenylethynyl)naphthalene15.3 g (43.6 mmol) of 1-iodo-4-bromonaphthalene and 7.25 g (5.3 mmol) of 4-n-propylphenylacetylene are initially introduced in 200 ml of NEt3, 170 mg (0.9 mmol) of copper(I) iodide and 600 mg (0.9 mmol) of bis-(triphenylphosphine)palladium(II) chloride are added, and the mixture is refluxed for 30 minutes.The batch is cooled, water and heptane are added, and the phases are separated.The organic phase is washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated in a rotary evaporator.The residue is purified by column chromatography (SiO2, heptane), and the further purification is carried out by recrystallisation from isopropanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With I2; n-butyllithium; In tetrahydrofuran; hexane; | Synthesis Example 11-Iodo-4-bromonaphthalene100 g (350 mmol) of 1,4-dibromonaphthalene are initially introduced in 1 l of THF, cooled to -70° C., and 235 ml of n-BuLi (1.6 M in hexane, 370 mmol) are added dropwise.After 1 h, 103 g of I2 (406 mmol) in 250 ml of THF are added dropwise, the mixture is stirred at -70° C. for a further 2 h, warmed to 0° C. and quenched by the addition of 50 ml (644 mmol) of aqueous NaHSO3 solution (w=39percent).The phases are separated, and the aqueous phase is extracted once with MTB.The combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated in a rotary evaporator.The residue is purified by column chromatography (SiO2, heptane), and the further purification is carried out by recrystallisation from isopropanol, giving 1-iodo-4-bromonaphthalene as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; for 0.5h;Reflux; | 15.3 g (43.6 mmol) of 1-iodo-4-bromonaphthalene and 7.25 g (5.3 mmol) of 4-n-propylphenylacetylene are initially introduced in 200 ml of NEt3, 170 mg (0.9 mmol) of copper(I) iodide and 600 mg (0.9 mmol) of bis-(triphenylphosphine)palladium(II) chloride are added, and the mixture is refluxed for 30 minutes. The batch is cooled, water and heptane are added, and the phases are separated. The organic phase is washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated in a rotary evaporator. The residue is purified by column chromatography (SiO2, heptane), and the further purification is carried out by recrystallisation from isopropanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100 g (350 mmol) of 1,4-dibromonaphthalene are initially introduced in 1 l of THF, cooled to -70° C., and 235 ml of n-BuLi (1.6 M in hexane, 370 mmol) are added dropwise. After 1 h, 103 g of I2 (406 mmol) in 250 ml of THF are added dropwise, the mixture is stirred at -70° C. for a further 2 h, warmed to 0° C. and quenched by the addition of 50 ml (644 mmol) of aqueous NaHSO3 solution (w=39percent). The phases are separated, and the aqueous phase is extracted once with MTB. The combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated in a rotary evaporator. The residue is purified by column chromatography (SiO2, heptane), and the further purification is carried out by recrystallisation from isopropanol, giving 1-iodo-4-bromonaphthalene as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | A solution of <strong>[63279-58-3]3-bromo-4-iodonaphthalene</strong> (3.33 g, 10 mmol) was dissolved in 15 ml of tetrahydrofuran,Cooled to -78 ° C, 4 mL of 2.5 M n-butyllithium was added dropwise, stirred at -78 ° C for 1 hour,A solution of 1.54 g (10 mmol) of intermediate 1 dissolved in tetrahydrofuran was slowly added dropwise,After the termination of the reaction at room temperature, MC and 2N HCl were added and the organic layer was extracted. Anhydrous magnesium sulfate to remove moisture in the organic layer, suction filtration,The compound obtained by concentrating the organic solution was treated with Hex: EA = 5: 1Of the eluate of the column,To give 2.76 g (76percent) of intermediate 2. | |
76% | <strong>[63279-58-3]1-bromo-4-iodonaphthalene</strong>(3.33 g, lOmmol) was dissolved in tetrahydrofuran (15 mE), and cooled to ?78° C. n-butyllithium (2.5 M, 4 mE) was added dropwise, and stirred at ?78° C. for 1 h. Intermediate 1(1.54 g, 10 mmol)10066] The organic layer was dried over anhydrous magnesium sulfate, suctioned under reduced pressure, and concentrated. The resultant compound was purified by column chromatography eluting with Hex:EA=5: 1, to obtain Intermediate 2 (2.76 g, 76percent).dissolved in tetrahydrofuran (30 mE) was slowly addeddropwise, and warmed to normal temperature. Afier thereaction was terminated, MC and 2N HC1 were added, andthe organic layer was extracted. | |
76% | <strong>[63279-58-3]1-bromo-4-iodonaphthalene</strong> (3.33 g, 10 mmol) was dissolved in tetrahydrofuran (15 ml), and cooled to ?78° C.n-butyllithium (2.5 M, 4 mE) was added dropwise, and stirred at ?78° C. for 1 h. Intermediate 1(1.54 g, 10 mmol)dissolved in tetrahydrofuran (30 mE) was slowly added dropwise, and warmed to normal temperature. Afier the reaction was terminated, MC and 2N HC1 were added, and the organic layer was extracted.The organic layer was dried over anhydrous magnesium sulfate, suctioned, and concentrated. The resultant compound was purified by column chromatography eluting withHex:EA=5:1, to obtain Intermediate 2 (2.76 g, 76percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene;Inert atmosphere; Reflux; | The 9 - anthracene boric acid (10mmol), 1 - bromo -4 iodine naphthalene (10mmol), potassium carbonate (30mmol), four-triphenylphosphine palladium (0.1mmol) are sequentially added to the toluene, ethanol, water in the mixed solution in the reaction temperature under the protection of nitrogen to reflux the reaction overnight. The reaction cooling to room temperature a large number of solid is separated out filtering for products obtained toluene baggy air dissolved completely after-filtration, filtrate cooling crystallization product is obtained 219 - 1 (yield 65percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate; In N,N-dimethyl-formamide; at 155℃; for 72h;Inert atmosphere; | General procedure: Bromo-3-chloro-5-methoxybenzene (10 mmol, 2.2 g)Diphenylamine (20 mmol, 3.34 g) was added to a 100 mL three-necked flask,A cuprous iodide (2 mmol, 0.4 g) was added under nitrogen,Potassium carbonate (20 mmol, 1.4 g),O-phenanthroline (2 mmol, 0.4 g),50 mL of DMF,Reaction was carried out at 155 ° C for 3 days;The resulting reaction product is subjected to extraction,The extracted organic phase was evaporated to dryness with ethanol,Then recrystallized from ethyl acetate and petroleum ether,To obtain 1.83 g of intermediate A-1, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; nitric acid; | 4-Bromo-1-iodonaphthalene reacts with mixed acid (mixture of concentrated nitric acid and mixed sulfuric acid) to form 4-bromo-1-iodo-2-nitronaphthalene, taking 37.8 g, 100 mmol of 4-bromo-1-iodo-2- Nitro-naphthalene was charged with toluene,In a three-necked flask of ethanol and water mixed solvent, naphthaleneboronic acid (17.2 g, 100 mmol), potassium carbonate (41.4 g, 300 mmol), tetrakistriphenylphosphine palladium (1.154 g, 1 mmol) were added under nitrogen, and the temperature was at the reflux temperature. Reaction 5h.After the reaction is completed, deionized water is added, and the organic phase is extracted and washed with water. The combined organic phases are dried and concentrated. The resulting crude product is passed through a silica gel column to give 5-bromo-7H-dibenzo[c,g]carbazole (27.6 g). The yield is 80percent). | |
With sulfuric acid; nitric acid; | 4-Bromo-1-iodonaphthalene and mixed acid (mixture of concentrated nitric acid and mixed sulfuric acid) produce 4-bromo-1-iodo-2-nitronaphthalene.37.8 g, 100 mmol of 4-bromo-1-iodo-2-nitronaphthalene was added to a three-necked flask equipped with a mixed solvent of toluene, ethanol, and water, and naphthaleneboronic acid (17.2 g, 100 mmol), potassium carbonate was added under nitrogen gas ( 41.4 g, 300 mmol)), tetrakistriphenylphosphine palladium (1.154 g, 1 mmol), reacted at reflux temperature for 5 h. After the reaction was completed, deionized water was added, the organic phase was extracted and washed with water, the combined organic phases were dried, and the resulting crude product was concentrated on a silica gel column to give the product Intermediate A-1 (27.6 g, yield 80percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With potassium carbonate; In tetrahydrofuran; water; toluene; at 70 - 80℃; for 3h;Inert atmosphere; | (5) Intermediate E is <strong>[63279-58-3]1-bromo-4-iodonaphthalene</strong> as the main raw material, and <strong>[63279-58-3]1-bromo-4-iodonaphthalene</strong> is added to a 500 ml three-neck bottle41.94 g was dissolved in 200 g of toluene, and a 30percent aqueous solution of potassium carbonate (105 g) was added under nitrogen protection. Palladium acetate or tris(dibenzylidene) was added.Acetone) dipalladium is a catalyst, with tert-butylphosphoric acid or n-butyldi(1-adamantyl)phosphine or tricyclohexylphosphine as the catalyst ligand.The temperature was raised to 70-80°C with a water bath, and the addition of 30 g of 3-nitro-2-pyridineboronic acid pinacol ester to 150 g of THF was started.After the solution was added dropwise for 3 hours, the TLC reaction was completed, and the target product was obtained by layering, washing with the solvent, and recrystallizing dichloroethane.E23.7g, yield 60percent; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With bis(eta3-allyl-mu-chloropalladium(II)); potassium carbonate; 5-norbornene-endo-2-carboxylic acid; XPhos; In acetonitrile; at 70℃;Inert atmosphere; Schlenk technique; | General procedure: To a 25mL of oven-dried Schlenk tube equipped with a magnetic stir bar was charged with [Pd(C3H5)Cl]2 (3.7mg 0.01mmol, 0.05 equiv), XPhos (10.5mg, 0.022mmol, 0.11 equiv), K2CO3 (69.1mg, 0.5mmol, 2.5 equiv), and dry CH3CN (1mL). After stirring for about 15minat r.t. under argon, a solution of aryl iodide 1 (0.24mmol, 1.2 equiv), alkylating reagent 2 (0.2mmol, 1.0 equiv), 5-Norbornene-2-carboxylic acid N4 (5.5mg, 0.04mmol, 0.2 equiv) in dry MeCN (1mL) was added, then heated to 70°C and stirred for 5?24h. The reaction was monitored by TLC, after completion of the reaction, the mixture was cooled to r.t., filtered through a thin pad of celite eluting with ethyl acetate (10mL), and the combined filtrate was concentrated in vacuo. The residue was directly purified by column chromatography on silica gel or purified by PTLC to give the desired product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With potassium carbonate; copper(II) sulfate; In 1,2-dichloro-benzene; at 200℃; for 12h; | 40 g of compound 1-5 (101.4 mmol), 87 g of <strong>[63279-58-3]1-bromo-4-iodonaphthalene</strong> (26.1 mmol), 367 mg of CuSO4 (3.01 mmol), and 28 g of K2C03 (202.8 mmol) were dissolved in 500 mL of dichlorobenzene, stuffed for 12 hours at 200°C. After completion of the reaction, the reaction solvent was removed by distillation, and the resulting product was dried and then purified by column chromatography to obtain 18 g of compound 3-1 (yield: 30percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With tris-(dibenzylideneacetone)dipalladium(0); bis[2-(diphenylphosphino)phenyl] ether; sodium t-butanolate; In toluene; at 50℃; for 8h;Inert atmosphere; | Add <strong>[63279-58-3]1-bromo-4-iodo-naphthalene</strong> (3.33 g, 10 mmol) to a 150 mL two-necked flask under nitrogen.4-bromo-1,2-benzenedithiol (2.21 g, 10 mmol),Sodium tert-butoxide (4.81 g, 50 mmol),Tris(dibenzylideneacetone)dipalladium (458 mg, 0.5 mmol),Bis(2-diphenylphosphinophenyl)ether (269 mg, 0.5 mmol) and 90 mL of toluene,The reaction was stirred for heating to 50 ° C for 8 hours.The reaction is completed,Extract the product with dichloromethane,Washing the organic phase with a saturated aqueous solution of sodium chloride,Evaporate the solvent under reduced pressure.The crude product was purified by column chromatography using petroleum ether as eluent.A white solid was obtained in 2.34 g, yield 55percent.The results of 1H NMR, 13C NMR, MS and elemental analysis indicated that the obtained compound was the object product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79.7% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; toluene; at 90℃; | In a 500-mL round-bottom flask reactor were placed (10-phenyl(d5)-anthracene-9-boronic acid (38.6 g, 127 mmol), <strong>[63279-58-3]1-bromo-4-iodonaphthalene</strong> (35.3 g, 106 mmol), tetrakis(triphenylphosphine)palladium (3.43 g, 3 mmol), and potassium carbonate (27.35 g, 197.9 mmol), followed by toluene (150 mL), tetrahydrofuran (150 mL), and water (60 mL). The reactor was heated to 90° C. before stirring overnight. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The organic layer thus formed was isolated, concentrated in a vacuum, and purified by column chromatography to afford <Intermediate 14-a>. (39.2 g, 79.7percent) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; for 5h;Inert atmosphere; Reflux; | 0.043 mol of the intermediate 1-1-1 was dissolved in 200 ml of a 1,4-dioxane solvent and stirred under nitrogen. add 0.043 mol of <strong>[63279-58-3]1-bromo-4-iodonaphthalene</strong>,0.129 mol of K2CO3, 0.43 mmol of tetrakis(triphenylphosphine)palladium,The temperature was raised to reflux reaction, and after 5 hours, the basic reaction of the starting material was confirmed by HPLC, and the reaction mixture was evaporated to dryness, and the residue was subjected to column chromatography to afford Intermediate 1-1-2 (yield: 65percent). |
65% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; for 5h;Inert atmosphere; Reflux; | Synthesis of intermediate 1-1-2:0.043 mol of the intermediate 1-1-1 was dissolved in 200 ml of 1,4-dioxane solvent.Stirring under nitrogen, and sequentially adding 0.043 mol of <strong>[63279-58-3]1-bromo-4-iodophthalene</strong>,0.129 mol of K2CO3, 0.00043 mol of tetrakis(triphenylphosphine)palladium, and the temperature was raised to reflux.After 5 hours, the basic reaction of the raw materials was determined by HPLC, and the reaction solution was dried under reduced pressure.The residue was subjected to column chromatography to give Intermediate 1-1-2 (yield: 65percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8.11 g | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In toluene; for 8h;Inert atmosphere; Reflux; | Under argon, the 85 - 6 - a (4.89 g, 15 mmol), 85 - 6 - b (4.76 g, 14.3 mmol), four (triphenylphosphine) palladium (0.35 g, 0.3 mmol), toluene (43 ml), sodium carbonate aqueous solution (2 M, 21 ml) added in the flask, reflux reaction for 8 hours, cooling to room temperature, toluene extraction, the organic phase with saturated salt water washing, drying of the organic phase, for column chromatography for purifying, to obtain the bromide 85 - 6 - c; will be 85 - 6 - c (8.11 g, 20 mmol), [...][...] (6.22 g, 24 mmol), 1, 1' - (diphenylphosphine) - ferrocene-- palladium dichloride (II) dichloromethane complex (0.49 g, 0.6 mmol), potassium acetate (5.90 g, 60 mmol) and 79 ml toluene at reflux 16 hours, cooling, adding 26 ml water, stirring 30 minutes, separating the organic phase, through the short diatomite filter bed, then [...] organic solvent, the obtained crude product in heptane/recrystallization in toluene, to obtain the solid 85 - 6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | Synthesis of intermediate 1-22-1:A format reagent was prepared, and 0.01 mol of <strong>[63279-58-3]1-bromo-4-iodophthalene</strong> and magnesium (0.4 mol) were added to 20 ml of tetrahydrofuran.Warming up to the reflux reaction,Slowly drip the remaining 0.09 mol of a <strong>[63279-58-3]1-bromo-4-iodophthalene</strong> tetrahydrofuran saturated solution for about 1 h.Nitrogen protection is available. Add 0.1 mol of triphenylchlorosilane to another three-neck bottle.Tetrahydrofuran is stirred evenly, protected by nitrogen, and cooled to -5 ° C.Transfer the prepared format reagent to the dropping funnel, slowly add dropwise, keep the temperature of the system not exceed 10 ° C, stir for 30 min after the addition, and then slowly increase to 25 ° C.After 5 hours, the reaction was completed, and a saturated aqueous solution of ammonium chloride was added dropwise to the reaction solution.After stirring for 5 min, dichloromethane was extracted, and the organic phase was decompressed and dried.The residue was subjected to column chromatography to give Intermediate 1-22-1 (yield: 52percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: A three neck round bottom flask, equipped with dropping funnel, reflux condenser and magnetic stir bar is charged with an arylhalide (1 eq) and corresponding boronic ester or acid (1.25 eq. per halogen atom in arylhalide), the flask is sealed with a rubber septum, evacuated and backfilled with argon (2 times). Anhydrous dioxane (4ml/mmol of arylhalide) is added through the septum using a double-tipped needle. Separately, a solution of potassium carbonate (2M in water) is prepared and degassed with N2for 30 min. The solution is added to the reaction mixture through the septum using a double-tipped needle, followed by the addition of thetetrakis(triphenylphosphin)palladium(0) (3mol percent) under a positive nitrogen pressure. Nitrogen purged reflux condenser is attached to the flask and the reaction mixture is stirred at 90°C for 12 h. The mixture is allowed to cool down to the room temperature, a precipitate is collected by filtration, washed with water, methanol, dried in vacuum at 40°C to give a crude product, which is further purified by re-crystallization or trituration with appropriate solvents. Final purification is achieved by sublimation in a high vacuum. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 70℃; for 11h;Inert atmosphere; | General procedure: 1-1 (35.92 g, 100.08 mmol), 1-2 (28.19 g, 100.08 mmol), was added to a 2 L reactor under nitrogen.Potassium carbonate (1.24 g, 9.00 mmol) and toluene (200 mL) were stirred.The temperature in the reaction vessel was raised to 70 ° C, and Pd(PPh3) 4 (1.04 g, 0.90 mmol) was added thereto, and 100 mL of distilled water was stirred, and the mixture was stirred under reflux for 11 hours to sufficiently react.After the reaction was terminated by adding 70 mL of distilled water, the mixture was filtered under reduced pressure, and the solid was washed with distilled water, and then recrystallized from acetone, toluene, and THF.After obtaining a solid, it is sublimed, and the toluene is recrystallized.Intermediate 1-3 31.13g is obtained,The yield was 80.44percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; toluene; for 10h;Inert atmosphere; Reflux; | Under argon atmosphere,7.61 g (22.86 mmol) of compound b-4,5.76 g (12 mmol) of intermediate C'-1,0.53 g (0.46 mmol) of tetrakistriphenylphosphine palladium dissolved in 35 ml of toluene,35 ml of dimethoxyethane and 35 ml of aqueous sodium carbonate (2M, 69 mmol),The reaction was refluxed for 10 hours,After completion of the reaction, the mixture was extracted with methylene chloride.Filtration, concentration, and purification by silica gel column chromatography.Finally, 5.11 g (8.0 mmol) of intermediate D'-1 was obtained.The yield was 70percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54.86% | With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 108℃; for 7h; | Intermediate II-I-1 (5.00 g, 10.25 mmol), <strong>[63279-58-3]1-bromo-4-iodophthalene</strong> (5.12 g, 15.38 mmol),Tris(dibenzylideneacetone)dipalladium (0.19 g, 0.21 mmol),Tri-tert-butylphosphine (0.08 g, 0.41 mmol) and sodium tert-butoxide (1.48 g, 15.38 mmol)Add toluene (50 mL), heat to 108 C under nitrogen, stir for 7 h;After cooling to room temperature, the reaction solution was filtered, and the filtrate was evaporated under reduced pressure;The obtained crude product was purified by silica gel column chromatography using dichloromethane/n-heptane (1:8) as mobile phase, and then the crude product was recrystallized and purified with dichloromethane/n-heptane.Obtained as an off-white solid intermediate II-I (3.61 g, 54.86%) |
Tags: 63279-58-3 synthesis path| 63279-58-3 SDS| 63279-58-3 COA| 63279-58-3 purity| 63279-58-3 application| 63279-58-3 NMR| 63279-58-3 COA| 63279-58-3 structure
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