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[ CAS No. 589-87-7 ] {[proInfo.proName]}

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Chemical Structure| 589-87-7
Chemical Structure| 589-87-7
Structure of 589-87-7 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 589-87-7 ]

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Product Details of [ 589-87-7 ]

CAS No. :589-87-7 MDL No. :MFCD00001051
Formula : C6H4BrI Boiling Point : -
Linear Structure Formula :- InChI Key :UCCUXODGPMAHRL-UHFFFAOYSA-N
M.W :282.90 Pubchem ID :11522
Synonyms :

Calculated chemistry of [ 589-87-7 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 46.86
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.39 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.34
Log Po/w (XLOGP3) : 3.71
Log Po/w (WLOGP) : 3.05
Log Po/w (MLOGP) : 3.95
Log Po/w (SILICOS-IT) : 3.54
Consensus Log Po/w : 3.32

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.49
Solubility : 0.00923 mg/ml ; 0.0000326 mol/l
Class : Moderately soluble
Log S (Ali) : -3.4
Solubility : 0.112 mg/ml ; 0.000397 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.2
Solubility : 0.0181 mg/ml ; 0.0000638 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.22

Safety of [ 589-87-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P273-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362+P364-P403+P233-P501 UN#:N/A
Hazard Statements:H315-H319-H335-H413 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 589-87-7 ]

* 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 [ 589-87-7 ]

[ 589-87-7 ] Synthesis Path-Downstream   1~80

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YieldReaction ConditionsOperation in experiment
94% With caesium tribromide; In water; N,N-dimethyl-formamide; at 80℃; for 5h; General procedure: To a solution of trifluoroborate (1 mmol) in 3 mL of aqueous DMF (2:1 v/v), cesium triiodide (1 mmol) was added. The mixture was stirred at 80 C for the appropriate time (Table 3) and then diluted with 10 mL of ether. The aqueous layer was extracted twice with ether (5 mL) and the combined organic phase was dried over anhydrous Na2SO4. After evaporation of the solvent the residue was purified by silica gel column chromatography [elute: hexane (or pentane)-ethyl acetate (or Et2O)].
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  • [ 18869-30-2 ]
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  • [ 288-32-4 ]
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  • [ 10040-96-7 ]
YieldReaction ConditionsOperation in experiment
94% With C40H34CuIN6O6; sodium hydroxide; In dimethyl sulfoxide; at 100℃; for 4h;Sealed tube; General procedure: For the catalysis reaction, the catalyst C1 (12 mg,0.01 mmol), imidazole (1.0 mmol), aryl halide(1.0 mmol), NaOH (80 mg, 2.0 mmol), and dimethylsulfoxide (DMSO, 5 mL) were taken in a sealed tube. The reaction mixture was stirred at 100 C for 4 h and then cooled to room temperature. After adding 5 mL of H2O, the solution was extracted with ethyl acetate. The organic layer was then dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure.The N-arylated product was finally obtained by columnchromatography on silica gel.
92% With copper(l) chloride; sodium hydroxide; 3-(diphenylphosphino)propionic acid; In dimethyl sulfoxide; at 120℃; for 14h;Inert atmosphere; Sealed tube; General procedure: NH-containing heterocycle (1.4 mmol) and DMF (2.0 mL) were added to a mixture of CuCl (15.0 mol%) and ligand 1 (20.0 mol%) in DMF (2.0 mL), aryl iodide (1.0 mmol), NaOH (2.0 mmol). The mixture was vigorously stirred at 120 C for 14 h under a dry nitrogen atmosphere. After completion of the reaction (as monitored by TLC), H2O was added and the organic layer was extracted with EtOAc, washed with brine and dried over MgSO4. The solution was filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography. The purity of the compounds was checked by 1H NMR and yields are based on aryl iodide. All the products are known and the spectroscopic data (FT-IR and NMR) and melting points were consistent with those reported in the literature.
82% With Cu/Al2O3; potassium hydroxide; In N,N-dimethyl-formamide; at 80℃;Green chemistry; General procedure: To equimolar amounts (0.1mmol) of the halide and the nitrogenated nucleophile in DMF were added KOH and the 3D heterogeneous Cu/Al2O3 catalytic system. The reaction mixture was heated at 80C under orbital stirring in a Kimble vial (7mL) for 2-4h. Once the reaction had finished (TLC control), the solvent was separated from the catalyst and this was successively washed with methanol and dichloromethane (5mL). The organic solvents were removed under vacuum and the residue was purified by column chromatography to afford the desired compound (2-4).
82% With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 1h;Catalytic behavior; General procedure: The reaction flask, containing 0.02 g Cu(II) nanocatalyst(contains 0.4 mol% of Cu(II)), imidazole (2.0 mmol),K2CO3 (1.0 mmol), and corresponding aryl halide(1.0 mmol) in 2.5 cm3 DMF, was immersed in a preheated oil bath and the reaction mixture was stirred under air atmosphere at 120 C until no further conversion of the starting aryl halide was observed by thin-layer chromatography(TLC). After completion of the reaction, the resulting mixture was allowed to cool to room temperature,and then the catalyst was separated out by an external permanent magnet, washed with ethyl acetate (EtOAc) anddried. The residue mixture was diluted by H2O and extracted with EtOAc (3 9 10 cm3). The extracted organic phases were dried over anhydrous Na2SO4, filtrated, concentrated and, finally, purified by silica gel chromatography using petroleum ether/ethyl acetate to afford the corresponding pure N-arylimidazole.
70% With potassium carbonate; In toluene; at 110℃; for 14h;Catalytic behavior; To a solution of N-H heterocycle (1 mmol) and aryl halide (2 mmol) in toluene were added catalyst (0.07 g, 0.016 mmol) and K2CO3 (276 g, 2 mmol) and the mixture stirred at 110 C for the specified time. The progress of the reaction was monitored by TLC. The reaction mixture allowed cooling to room temperature and ethyl acetate (25 mL) was added and the mixture stirred for 15 min to ensure product removal from catalyst. Then the catalyst was filtered, washed with ethyl acetate (2 9 25 mL). The organic layer was evaporated under vacuum on a rotary evaporator and the crude product was obtained. Further purification was achieved by column chromatography using ethyl acetate/n-hexane gradient. Structural assignments of the products are based on their 1H NMR and melting point.

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  • 4'-bromo-5,6-dimethoxy-biphenyl-3-carbaldehyde [ No CAS ]
  • 14
  • [ 123-75-1 ]
  • [ 589-87-7 ]
  • [ 22090-26-2 ]
YieldReaction ConditionsOperation in experiment
50.17% With copper(l) iodide; caesium carbonate; L-proline; In N,N-dimethyl-formamide; at 120℃; for 10h;Inert atmosphere; Compound BB-4D-1 (10.00 g, 35.35 mmol) and pyrrolidine (2.77 g, 38.89 mmol) were dissolved in N,N-dimethylformamide (100 mL) at room temperature under nitrogen atmosphere, followed by addition of cuprous iodide (673.24 mg, 3.54 mmol), L-proline (813.97 mg, 7.07 mmol) and cesium carbonate (13.82 g, 42.42 mmol). After completion of the addition, the reaction mixture was heated to 120 C and stirred for 10 hours under nitrogen atmosphere. After completion of the reaction, the mixture was cooled to room temperature, quenched with saturated brine (200 mL), and extracted with ethyl acetate (500 mL × 3). The organic phases were combined, washed with water (200 mL), dried over anhydrous sodium sulfate, filtered to remove the desiccant and concentrated under reduced pressure. The insoluble material was removed by filtration, and the obtained residue was purified by silica gel column chromatography (eluent: petroleum ether) to obtain the title compound BB-4D-2 (white solid, 4.01 g, yield: 50.17%). 1H NMR (400MHz,CDCl3) delta: 7.29 (d, J = 9.0 Hz, 2H), 6.43 (d, J = 9.0 Hz, 2H), 3.25 (t, J = 6.7 Hz, 4H), 2.01 (td, J = 3.4, 6.6 Hz, 4H).
With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 80℃;Inert atmosphere; Example 23: 2-Chloro-5-(4-pyrrolidin-1-yl-benzoyl)-benzenesulfonamide; 1 -(4-Bromo-phenyl)-pyrrolidine ;A oven-dried 50 ml_ of round bottom flask is charged with Pd2(dba)3 (116 mg, 0.13 mmol), BINAP (158 mg, 0.25 mmol), and sodium tert-butoxide (916 mg, 9.54 mmol). The flask is evacuated and backfilled with argon. Degassed toluene (5 ml_), 1-iodo-4- bromobenzene (1.8 g, 6.36 mmol), pyrrolidine (542 mg, 7.63 mmol) are then added. The mixture is heated at 80 0C until the starting aryl iodide is completed consumed judged by LC- MS analysis. The mixture is diluted with ethyl acetate, filtered through Celite, and concentrated in vacuo. The crude product is purified by flash chromatography to give 1.1 g of product as light brown solid. 1H NMR (400 MHz, CDCI3): delta 2.00 (t, 4H, J =4 Hz), 3.24 (t, 4H, J =4Hz), 6.42 (d, 2H, J = 8 Hz), 7.29 (d, 2H, J = 8 Hz).
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  • [ 589-87-7 ]
  • [ 106-94-5 ]
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  • [ 589-87-7 ]
  • [ 1692-15-5 ]
  • [ 39795-60-3 ]
YieldReaction ConditionsOperation in experiment
80% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 12h;Inert atmosphere; The compound 1-bromo-4-iodobenzene (20 g, 104.5 mmol) was dissolved in 0.5 L of tetrahydrofuran (THF) in a nitrogen atmospherePyridin-4-yl-boronic acid (15.4 g, 125.4 mmol) and tetrakis (triphenylphosphine) palladium (1.2G, 1 mmol) were added and stirred. Saturated water-saturated potassuim carbonate (17.3 g, 125.4 mmol) was added and heated to 80 CThe mixture was heated to reflux for a period of time. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM)The water was removed with MgSO4, filtered and concentrated under reduced pressure. The residue thus obtained was purified by flash column chromatographySeparation and purification were conducted to obtain the compound I-6 (15 g, 80%).
58% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 20 - 110℃; for 24.166h;Inert atmosphere; Specifically: under argon protection, p-bromoiodobenzene (3.4 g, 12 mmol), 4-pyridineboronic acid (1.3 g, 10 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mol) and sodium carbonate (3.2 g, 30 mmol) was added to a 250 mL three-neck bottle. After adding toluene (100 mL), ethanol (30 mL) and water (10 mL), the mixture was evaporated, and then stirred at room temperature for 10 minutes, then heated to reflux to 110 C and stirred for 24 h. Then, it was filtered, concentrated, extracted with saturated brine, dried, and purified by column chromatography to give the product 4-pyridinebromobenzene (yield 58%).
With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 80℃; EXAMPLE 3; Synthesis of (2S)-N-(cyanomethyl)-4-methyl-2-[(R)-phenyl(4'-pyridin-4-yl-1,1'-biphenyl-4-yl)methyl]oxy} pentanamide; Step 1 4-(4-bromophenyl)pyridine; Pyridin-4-ylboronic acid (500 mg, 4.07 mmol), 1-bromo-4-iodobenzene (1.27g, 4.47 mmol) and 2M Na2CO3 (6.1 ml, 12.2 mmol) were dissolved in 20 ml DMF and the solution was degassed 3 times. PdCl2(dppf) (149mg, 0.203 mmol) was added and the mixture was stirred overnight at 80C. The solution was cooled, poured into 100 ml NaHCO3 (sat.) and extracted 3 times with 20ml ethyl acetate. The combined organic layers were then washed with 4 x water, then dried with Na2SO4. 4-(4-bromophenyl)pyridine was obtained and used without further purification.
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  • [ 955959-84-9 ]
YieldReaction ConditionsOperation in experiment
93% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 8h;Inert atmosphere; In a nitrogen atmosphere, dibenzofuran-4-ylboronic acid (100 g, 472 mmol) was dissolved in 1,000 mL of tetrahydrofuran (THF)1-bromo-4-iodobenzene (160 g, 556 mmol) and tetrakis (triphenylphosphine) palladium (5.45 g, 4.72 mmol) were added thereto and stirred.Potassium carbonate (78.3 g, 566 mmol) saturated with water was added and the mixture was refluxed by heating at 80 ° C for 8 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM). Then, water was removed with anhydrous MgSO 4,Filtered and concentrated under reduced pressure.The thus-obtained residue was purified by flash column chromatography to obtain Compound I-9 (142 g, 93percent).
89% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 12h;Reflux; Inert atmosphere; To a round bottom flask, 4-dibenzofuran boronic acid 20g (94.3mmol), 1- bromo-4-iodo benzene  26.7g (94.3mmol) was put and toluene (313ml) mmol) was added and dissolved and then an aqueous solution 117ml of potassium carbonate 19.5g (141.5 mmol)dissolved was added and stirred. Here, tetrakis triphenylphosphine palladium 1.09g (0.94mmol)was added and stirred under reflux for 12 hours under a nitrogen atmosphere.After the end of the reaction and the extract was extracted to ethyl acetate, the extract was dried and filtered through magnesium sulfate, and the filtrate was concentrated under reduced pressure.The product n- hexane / dichloromethane (9: 1 volumetric ratio) was purified by silica gel column chromatography to give the 27g (89percentyield) of the aimed compound intermediate M-1 as a white solid.
89% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 12h;Inert atmosphere; Reflux; 4-dibenzofuran boronic acid 20g (94.3mmol) in a round bottom flask, 1-bromo-4-iodo benzene, 26.7g (94.3mmol) And stirred into 117ml aqueous solution was added to dissolve the potassium carbonate and 19.5g (141.5mmol) was dissolved was added to toluene (313ml). Followed by adding thereto tetrakis triphenylphosphine palladium 1.09g (0.94mmol) was stirred under reflux for 12 hours under a nitrogen atmosphere. After the end of the reaction the extract was concentrated to dryness and extracted with ethyl acetate and filtered through a magnesium sulfate, and the filtrate under reduced pressure. The product n- hexane / dichloromethane (9: 1 by volume) was purified by a silica gel column chromatography to give the intermediate M-1 as a white solid 27g (89percent yield).
89% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 12h;Reflux; Inert atmosphere; 4-dibenzofuran boronic acid 20g (94.3mmol) and 1-bromo-4-iodo benzene 26.7g(94.3mmol) in toluene (313 ml) was added in a round bottom flask and stirred, an aqueous solution (117 ml) of potassium carbonate 19.5g (141.5mmol) was added, followed by adding tetrakistriphenylphosphine palladium 1.09g (0.94mmol) and stirred under reflux for 12 hours under a nitrogen atmosphere. After the end of the reaction, the reaction mixture was extracted with ethyl acetate, dried using magnesium sulfate, and the filtrate was concentrated under reduced pressure. The obtained product was purified by silica gel column chromatography using n-hexane/dichloromethane (9: 1 by volume) to give the desired intermediate compound M-1 27g (89percent yield) as a white solid.
89% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; for 12h;Inert atmosphere; Reflux; 4-benzofuran boronic acid (4-dibenzofuranboronic acid) 20g (94.4mmol), 1- bromo-4-iodo-benzene 28g (99.2mmol) and tetrakistriphenylphosphine palladium flask 1.08g (0.94mmol) put in was dissolved in 240ml of toluene and 120mL of ethanol under a nitrogen atmosphere after the addition of an aqueous solution of potassium carbonate dissolved in 120ml 28g (188.8mmol) it was stirred under reflux for 12 hours. After the reaction the extract was dried, filtered and then extracted with ethyl acetate and with magnesium sulfite and concentrated under reduced pressure of the filtrate. The product n- hexane / dichloromethane (9: 1 by volume) as the desired compound of intermediate M-9 was purified by silica gel column chromatography to give a 27g (89percent yield) as a white solid.
89% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 12h;Inert atmosphere; Reflux; Will be 20 grams (94.3 millimoles) 4-dibenzofuran boric acid and 26.7 g (94.3 mmol) 1-Bromo-4-iodobenzene was placed in a round bottom flask, and 313 ml of toluene was added thereto to dissolve it. A 117 ml aqueous solution obtained by dissolving 19.5 g (141.5 mmol) of potassium carbonate was added thereto, and the mixture was agitated. Subsequently, 1.09 g (0.94 mmol) of tetratriphenylphosphine palladium was added thereto. The resulting mixture was refluxed under a nitrogen atmosphere and stirred for 12 hours. When the reaction was completed, the resultant was extracted with ethyl acetate. The extracted solution was dried over magnesium sulfate and filtered. The filtered solution was concentrated under reduced pressure. Subsequently, the product obtained therefrom was treated with n-hexane/dichloromethane (9:1 vol/vol) Purified by gel column chromatography, Obtained 27 g of intermediate M-1 as a white solid (yield: 89percent).
81% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; toluene; for 10h;Inert atmosphere; Reflux; [Production Example 1] Synthesis of 4-(4-bromophenyl)dibenzofuran Under an argon atmosphere, 300 mL of toluene and 150 mL of a 2-M aqueous solution of sodium carbonate were added to 28.3 g (100 mmol) of 4-iodobromobenzene, 22.3 g (105 mmol) of dibenzofuran-4-boronic acid, and 2.31 g (2.00 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was refluxed under heat for 10 hours. Immediately after the completion of the reaction, the resultant was filtrated, and then the water layer was removed. The organic layer was dried with sodium sulfate, and was then concentrated. The residue was purified by silica gel column chromatography, whereby 26.2 g of the white crystal of 4-(4-bromophenyl)dibenzofuran were obtained (81percent yield).
81% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; for 10h;Reflux; Inert atmosphere; <Synthesis Example 5 (Synthesis of Intermediate 5)>; Under the atmosphere of argon gas, 300 ml of toluene and 150 ml of 2 M concentration sodium carbonate aqueous solution was added to 28.3 g (100 mmol) of 4-iodobromobenzene, 22.3 g (105 mmol) of dibenzofurazi-4-boronic acid and 2.31 g (2. 00 mmol) of tetrakis(triphenylphosphine)palladium (0), and the resultant mixture solution was heated while refluxing for 10 hours. After the reaction was completed, filtration was carried out immediately and a water layer was removed. After drying the organic layer over sodium sulfate, the resultant was concentrated. The residue was subjected to a chromatography purification using a silica gel column to obtain 26.2 g of 4-(4-bromophenyl)dibenzofuriran in the state of a white crystal (yield:81percent). The resultant white crystal was identified as Intermediate 5 from the result in accordance with the FD-MS analysis.
81% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; toluene; for 10h;Inert atmosphere; Reflux; In an argon atmosphere, 150 ml of toluene, 150 ml of dimethoxyethane, and 150 ml (300.0 mmol) of a 2 M aqueous solution of Na2CO3 were added to a mixture of 28.3 g (100.0 mmol) of 4-iodobromobenzene, 22.3 g (105.0 mmol) of dibenzofuran-4-boronic acid and 2.31 g (2.00 mmol) of Pd[PPh3]4, and the resultant mixture was stirred for 10 h while refluxing under heating. [0160] After the reaction, the reaction product extracted with dichloromethane in a separatory funnel. The organic layer was dried over MgSO4, filtered, and then concentrated. The concentrate was purified by silica gel column chromatography, to obtain 26.2 g of a white solid, which was identified as the following intermediate 1-5 by FD-MS analysis (yield: 81percent).
81% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; toluene; for 10h;Inert atmosphere; Reflux; [0184] In an argon atmosphere, 28.3 g (100.0 mmol) of 4-iodobromobenzene, 22.3 g (105.0 mmol) of dibenzofuran-4-boronic acid and 2.31 g (2.00 mmol) of Pd[PPh3]4 were added with 150 ml of toluene, 150 ml of dimethoxyethane and150 ml (300.0 mmol) of a 2 M aqueous solution of Na2CO3. The resultant mixture was stirred for 10 h while refluxingunder heating.[0185] After the reaction, the mixture was extracted with dichloromethane in a separatory funnel. The organic layerwas dried over MgSO4, filtered, and then concentrated. The concentrate was purified by silica gel column chromatographyto obtain 26.2 g of white solid, which was identified as the following intermediate 1-4 by FD-MS (yield: 81percent)
81% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; toluene; for 10h;Inert atmosphere; Reflux; INTERMEDIATE SYNTHESIS 1-1 (Synthesis of intermediate 1-1) [0106] Under an argon atmosphere, into a mixture of 28.3 g (100.0 mmol) of 4-iodobromobenzene, 22.3 g (105.0 mmol) of dibenzofuran-4-boronic acid, and 2.31 g (2.00 mmol) of Pd[PPh3]4, 150 ml of toluene, 150 ml of dimethoxyethane, and 150 ml (300.0 mmol) of a 2 M aqueous solution of Na2CO3 were added, and the resultant mixture was stirred for 10 h while refluxing under heating. [0107] After the reaction, the obtained mixture was cooled to room temperature and extracted with dichloromethane in a separatory funnel. The organic layer was dried over MgSO4, and then filtered and condensed. The condensate was purified by silica gel column chromatography to obtain 26.2 g of a white solid, which was identified as the intermediate 1-1 by FD-MS analysis (Field Desorption Mass Spectrometry Analysis) (yield: 81percent).
81% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; toluene; for 10h;Inert atmosphere; Reflux; INTERMEDIATE SYNTHESIS 2-1 (Synthesis of intermediate 2-1)[0105] Under an argon atmosphere, 150 ml of toluene, 150 ml of dimethoxyethane, and 150 ml (300.0 mmol) of a 2M aqueous solution of Na2CO3 were added to a mixture of 28.3 g (100.0 mmol) of 4-iodobromobenzene, 22.3 g (105.0mmol) of dibenzofuran-4-boronic acid, and 2.31 g (2.00 mmol) of Pd[PPh3]4, and the resultant mixture was stirred for10 h while refluxing under heating.[0106] After the reaction, the obtained mixture was cooled to room temperature and extracted with dichloromethanein a separatory funnel. The organic layer was dried over MgSO4, and then filtered and concentrated. The concentratewas purified by silica gel column chromatography to obtain 26.2 g of a white solid, which was identified as the intermediate2-1 by FD-MS analysis (yield: 81percent).
81% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; toluene; for 10h;Inert atmosphere; Reflux; In the argon atmosphere, are respectively weighing 4-iodo-bromobenzene 28.3g (100.0mmol), dibenzofuran-4-boronic acid 22.3g (105.0mmol), Pd[PPh3]42.31g (2.00mmol), adding toluene 150 ml, dimethoxy ethane 150 ml and 2M the Na2CO3aqueous solution 150 ml (300.0mmol), heating to reflux stirring 10 hours.After the reaction, cooling to room temperature, the reaction mixture is transferred to the separatory funnel, using dichloromethane extract. The organic layer using MgSO4dried, filtered and concentrated. The concentrated residue is purified with silica gel column chromatography, thereby obtaining 26.2g white solid (yield 81percent).
81% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; toluene; for 10h;Inert atmosphere; Reflux; Under an argon atmosphere, toluene (150 mL), dimethoxyethane (150 mL), and an aqueous solution of sodium carbonate having a concentration of 2 M (150 mL) were added to 4-iodobromobenzene (28.3 g, 100.0 mmol), dibenzofuran-4-boronic acid (22.3 g, 105 mmol), and tetrakis(triphenylphosphine)palladium(0) (2.31 g, 2.00 mmol), and then the mixture was heated for 10 hours while being refluxed. Immediately after the completion of the reaction, the resultant was filtrated, and then the aqueous layer was removed. The organic layer was dried with sodium sulfate, and was then concentrated. The residue was purified by silica gel column chromatography. Thus, an intermediate body 3H-1 (26.2 g, 81percent yield) was obtained. FD-MS (field desorption mass spectrometry) analysis confirmed that the intermediate had a ratio m/e of 322 with respect to its molecular weight, i.e., 322.
81% To a round bottom flask was added dibenzofuran-4-boronic acid (1.6 g, 5 mmol),4-iodobromobenzene (1.35 g, 4.76 mmol), sodium carbonate (1.48 g, 2M)toluene (50 ml) was added thereto, followed by stirring for 20 minutes. Tetrakis (triphenylphosphine) palladium (0) (0.11 g, 0.095 mmol) was added and the mixture was refluxed for 4 hours.After confirming with HPLC and LC-MASS, the reaction was terminated. After removal of the solvent, it was extracted with MC / H2O. column (MC: Hex = 1: 4) and reprecipitated with MC / hexane to obtain a solid compound (1.24 g, yield = 81percent).
75.7% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water;Reflux; To a round bottom flask was dissolved 20.0 g of dibenzofuran-4-boronic acid, 26 g of 4-bromo-1-iodo-benzene and 200 ml of 1,4-dioxane 40 ml of K2CO3 (2M) and 40 ml of Pd (PPh3) 4And the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure and purified to obtain 23 g (yield: 75.7percent) of intermediate OP3 (4-(4-bromophenyl)dibenzo[b,d]furan)23g (yield: 75.7percent).
56% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 70 - 80℃; for 3h; Preparation of compound C-6-1 [133] After dissolving dibenzo[b,d]furan-4-yl boronic acid (20 g, 94.34 mmol), 1-bromo-4-iodo-benzene (53.4 ml, 188.68 mmol), Pd(PPh3)4 (5.45 g, 4.72 mmol) and K2CO3 (39.1 g, 283.01 mmol) in a mixture of toluene (900mL), EtOH (200mL) and distilled water (200mL), the reaction mixture was stirred for 3 hours at 70~80°C. After terminating the reaction, an aqueous layer was removed from the mixture by a gravity separation. And then, the obtained organic layer was concentrated and purified through column to obtain compound C-6-1 (17 g, 56 percent).
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 90℃; for 2 - 3h; A solution of dibenzofuran-4-boronic acid (1.0 g, 4.7 mmol) in ethanol (10 ML) was added to a stirred solution of 1- bromo-4-iodobenzene (1.33 g, 4.7 mmol) and tetrakis- (triphenylphosphine) palladium (0) (271 mg, 5 MOLpercent) in toluene (40 mL). 2N sodium carbonate (4.7 mL, 9.4 mmol) was added and the reaction was heated to 90°C (oil bath temp. ) for 2-3 hrs until complete (TLC control). The reaction mixture was cooled to room temperature and partitioned between water and diethyl ether. The phases were separated, the aqueous phase being further extracted with diethyl ether (2 x 20 mL). The combined extract was washed with water and brine. The ethereal solution was dried over anhydrous MGS04, filtered and concentrated in vacuo to yield 4- (4-BROMOPHENYL)-DIBENZOFURAN as a yellow solid, which was used immediately without further purification. A solution of 4-FORMYLPHENYLBORONIC acid (0.9 g, 5.64 mmol) in ethanol (10 mL) was added to a stirred solution of the crude 4- (4-BROMOPHENYL)-DIBENZOFURAN (from the previous reaction) in toluene (40 mL). tetrakis- (Triphenylphosphine) palladium (0) (270 mg, 5 molpercent) and 2N sodium carbonate (4.7 mL, 9.4 mmol) were added and the reaction was heated to 100°C (oil bath temp. ) for 2-3 hrs until complete (TLC control). The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The phases were separated, the aqueous phase being further extracted with ethyl acetate (2 x 20 mL). The combined extract was washed with 0.5 N hydrochloric acid, water and brine and then dried over anhydrous MGS04, filtered and concentrated in vacuo. Purification of the product by flash column chromatography, using 10-20percent ethyl acetate in hexane as eluent, afforded the title compound has a white solid (1.51g).
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 90℃; for 2 - 3h; Example 7. 4' -Dibenzofuran-4-yl-biphenyl-4-carbaldehyde; EPO <DP n="91"/> A solution of dibenzofuran-4-boronic acid (1.0 g, 4.7 mmol) in ethanol (10 iriL) was added to a stirred solution of 1- bromo-4-iodobenzene (1.33 g, 4.7 mmol) and tetrakis- (triphenylphosphine)palladium(O) (271 mg, 5 molpercent) in toluene (40 mL) . 2N sodium carbonate (4.7 mL, 9.4 mmol) was added and the reaction was heated to 900C (oil bath temp.) for 2-3 hrs until complete (TLC control) .The reaction mixture was cooled to room temperature and partitioned between water and diethyl ether. The phases were separated, the aqueous phase being further extracted with diethyl ether (2 x 20 mL) . The combined extract was washed with water and brine. The ethereal solution was dried over anhydrous MgSO4, filtered and concentrated in vacuo to yield 4- (4-bromophenyl) -dibenzofuran as a yellow solid, which was used immediately without further purification.A solution of 4-formylphenylboronic acid (0.9 g, 5.64 mmol) in ethanol (10 mL) was added to a stirred solution of the crude 4- (4-bromophenyl) -dibenzofuran (from the previous reaction) in toluene (40 mL) . tetrakis-(Triphenylphosphine)palladium(O) (270 mg, 5 molpercent) and 2N sodium carbonate (4.7 mL, 9.4 mmol) were added and the reaction was heated to 1000C (oil bath temp.) for 2-3 hrs until complete (TLC control) . The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The phases were separated, the aqueous phase being further extracted with ethyl acetate (2 x 20 mL) . The combined extract was washed with 0.5 N hydrochloric acid, water and brine and EPO <DP n="92"/>then dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification of the product by flash column chromatography, using 10-20percent ethyl acetate in hexane as eluent, afforded the title compound has a white solid (1.5Ig) .
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 90℃; for 2 - 3h; Example 1; 2-tert-Butoxycarbonylamino-3- (4 ' -dibenzofuran-4-yl-biphenyl-4- ylmethylsulfanyl) -propionic acid; Step 1; Preparation of 4' -Dibenzofuran-4~yl-biphenyl-4- carbaldehyde; A solution of dibenzofuran-4-boronic acid (1.0 g, 4.7 mmol) in ethanol (10 mL) was added to a stirred solution of 1- bromo-4-iodobenzene (1.33 g, 4.7 mmol) and tetrakis- (triphenylphosphine) -palladium(0) (271 mg, 5 molpercent) in toluene (40 mL) . 2 N sodium carbonate (4.7 mL, 9.4 mmol) was added and then the reaction was heated to 90 0C (oil bath temp.) for 2-3 h until complete (TLC control) . The reaction mixture was cooled to room temperature and partitioned between water and diethyl ether. The phases were separated, the aqueous phase being further extracted with diethyl ether (2 x 20 mL) . The combined organic extracts were washed with water and sat'd aq NaCl. The ethereal solution was dried over anhyd MgSC>4, filtered and concentrated in vacuo to yield 4- (4-bromophenyl) - dibenzofuran as a yellow solid, which was used immediately without further purification.A solution of 4-formylphenylboronic acid (0.9 g, 5.64 mmol) in ethanol (10 mL) was added to a stirred solution of the crude 4- (4-bromophenyl) -dibenzofuran (from the previous EPO <DP n="111"/>reaction) in toluene (40 mL) . Tetrakis- (Triphenylphosphine) - palladium(0) (270 mg, 5 molpercent) and 2 N sodium carbonate (4.7 mL, 9.4 mmol) were added and then the reaction was heated to 100 0C (oil bath temp.) for 2-3 h until complete (TLC control) . The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The phases were separated, the aqueous phase being further extracted with ethyl acetate (2 x 20 mL) . The combined organic extracts were washed with 0.5 N hydrochloric acid, water and sat'd aq NaCl and then dried over anhyd MgSO4, filtered and concentrated in vacuo. Purification by flash column chromatography (10-20percent ethyl acetate in heptane) afforded the title compound has a white solid (1.5Ig) .
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 80℃; for 8h;Inert atmosphere; Synthesis Example 10 (synthesis of Intermediate 10); Under an argon stream, 536 g of commercially-available 4-dibenzofuranboronic acid, 600 g of 4-iodobromobenzene, 41 g of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4), 2.6 L of 2 M sodium carbonate (Na2CO3) solution, and 10 L of dimethoxyethane were charged, and the mixture was reacted at 80°C for 8 hours. The reactant was extracted with toluene and water, followed by drying with anhydrous sodium sulfate. The resultant was concentrated under reduced pressure, and the obtained crude product was subjected to column purification, whereby 257 g of white powder was obtained. By an FD-MS analysis, the white powder was identified as Intermediate 10.
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; for 10h;Inert atmosphere; Reflux; Under an argon atmosphere, 300 mL of toluene and 150 mL of an aqueous solution of sodium carbonate having a concentration of 2 M were added to 28.3 g of 4-iodobromobenzene, 22.3 g of dibenzofuran-4-boronic acid, and 2.31 g of tetrakis (triphenylphosphine) palladium (0), and then the mixture was heated while being refluxed for 10 hours. Immediately after the completion of the reaction, the resultant was filtrated, and then the aqueous layer was removed. The organic layer was dried with sodium sulfate, and was then concentrated. The residue was purified by silica gel column chromatography. Thus, 26.2 g of a white crystal were obtained. The crystal was identified as the Intermediate 21 by FD-MS analysis.
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; for 10h;Inert atmosphere; Reflux; Under an argon atmosphere, 300 mL of toluene and 150 mL of a 2 mol/L aqueous solution of sodium carbonate were added to 28.3 g of 4-iodobromobenzene, 22.3 g of dibenzofuran-4-boronic acid, and 2.31 g of tetrakis(triphenylphosphine)palladium, and then the mixture was heated for 10 hours while being refluxed. Immediately after the completionof the reaction, the resultant was filtrated, and then the aqueous layer was removed. The organic layer was dried with sodium sulfate, and was then concentrated. The residue was purified by silica gel column chromatography. Thus, 26.2 g of a white crystal were obtained. The white crystal was identified as the intermediate 3 by FD-MS analysis.
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; toluene; for 10h;Inert atmosphere; Reflux; Under argon atmosphere, 150 ml of toluene, 150 ml of dimethoxyethane and 150 ml (300.0 mmol) of a 2M aqueous solution of Na2CO3 were added to 28.3 g (100.0 mmol) of 4-iodobromobenzene and 22.3 g (105.0 mmol) of dibenzofuran-4-boronic acid and 2.31 g (2.00 mmol) of Pd[PPh3]4. The resulting mixture was heated under reflux while stirring for 10 hours.After the reaction was completed, the sample was transferred to a separating funnel, followed by extraction with dichloromethane. The organic layer was dried with MgSO4, followed by filtration and concentration. The concentrated residue was purified by silica-gel column chromatography to obtain 26.2 g of white solids. The solids were identified as Intermediate 12 by FD-MS analysis.
28.5 g With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In toluene; at 80℃; for 8h;Inert atmosphere; A three neck flask of 1000 ml was charged with 42.4 g of 4-dibenzofuranboronic acid, 56.0 g of 4-iodobromobenzene, 6.9 g of tetrakis-(triphenylphosphine)palladium (Pd(PPh3)4), 320 mL of a sodium carbonate (Na2CO3) solution of 2M and 320 mL of toluene under argon flow, and then they were reacted at 80° C. for 8 hours. The reaction solution was extracted with toluene/water, and the extract was dried on anhydrous sodium sulfate. This was concentrated under reduced pressure, and a crude product obtained was refined through a column, whereby 28.5 g of a white powder was obtained.
27 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; for 12h;Inert atmosphere; 20 g (94.4 mmol) of 4-dibenzofuranboronic acid, 28 g (99.2 mmol) of 1-bromo-4-iodobenzene, and 1.08 g (0.94 mmol) of tetrakistriphenylphosphine palladium were dissolved in 240 ml of toluene and 120 ml of ethanol under a nitrogen atmosphere in a flask, 120 ml of an aqueous solution in which 28 g (188.8 mmol) of potassium carbonate was dissolved was added thereto, and the mixture was agitated for 12 hours while being refluxed. When the reaction was complete, the resultant was extracted with ethyl acetate, the extracted solution was dried with magnesium sulfite and filtered, and the filtered solution was concentrated under a reduced pressure. The concentrated product was purified with n-hexane/dichloromethane (9:1 of a volume ratio) through silica gel column chromatography, obtaining 27 g of a white solid compound, an intermediate M-9 (89percent of a yield).
5.92 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 100℃; for 24h; In the 250 mE rounded-bottom flask, the compoundF 1(3.00 g, 14.15 mmol), the compoundA4 (4.00 g, 14.15mmol), tetrakis(triphenylphosphine)palladium(0) (0.82 g,0.71 mmol) and potassium carbonate (4.84 g, 35.00 mmol)were put into a mixture of toluene (70 mE), ethanol (35 mE)and water (17.5 mE) and stirred under the temperature of100° C. for 24 irs. Afier the completion of the reaction, the mixture was extracted and condensed using water and dichloromethane. The mixture was separated by a column using dichloromethane and n-hexane and precipitated using dichloromethane and petroleum ether. The precipitate was filtered such that the compound F2 was obtained. (5.92 g, 25.29 mmol)
3.95 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 100℃; for 24h; To a 250 mL round bottom flask was added G1 (3.00 g, 14.15 mmol),G2 (4.00 g, 14.15 mmol), tetrakis (triphenylphosphine) palladium (0) (0.82 g, 0.71 mmol) and potassium carbonate (4.84 g, 35.00 mmol) were dissolved in toluene (80 mL) Ethanol (20 mL) and water (20 mL) were added to the mixed solution,And the mixture was stirred at 100 DEG C for 24 hours. After completion of the reaction,Water and dichloromethane were used for extraction and concentration,The column was separated using dichloromethane and n-hexane.Then, the precipitate was prepared by using dichloromethane and petroleum ether, Filtration gave Compound G3 (3.95 g, 12.22 mmol).
3.95 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 100℃; for 24h; Dibenzofuran-4-boronic acid (3.00 g, 14.15 mmol), 1-bromo-4-iodobenzene (4.00 g, 14.15 mmol) and tetrakis (triphenylphosphine) palladium (0) (0.82 g, 0.71 mmol) in a 250 mL round- and potassium carbonate (4.84 g, 35.00 mmol) were added to a mixed solution of Toluene (80 mL), Ethanol (20 mL) and water (20 mL) and stirred at 100 ° C for 24 hours. After completion of the reaction, the reaction mixture was extracted with water and dichloromethane, concentrated, and then subjected to column separation using dichloromethane and n-hexane. Thereafter, a precipitate was prepared using dichloromethane and petroleum ether, and filtered to obtain Compound D1 (3.95 g, 12.22 mmol).
3.95 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 100℃; for 24h; Dibenzofuran-4-boronic acid (3.00 g, 14.15 mmol), 1-bromo-4-iodobenzene (4.00 g, 14.15 mmol), tetrakis (triphenylphosphine) palladium (0) (0.82 g, 0.71 mmol)Potassium carbonate (4.84 g, 35.00 mmol) was dissolved in toluene (80 mL)Was added to a mixed solution of ethanol (20 mL) and water (20 mL), and the mixture was stirred at 100 ° C for 24 hours. After completion of the reaction, the reaction mixture was extracted with water and dichloromethane,The mixture was concentrated, and the column was separated using dichloromethane and n-hexane.Then, the precipitate was prepared by using dichloromethane and petroleum ether,Filtration gave Compound G1 (3.95 g, 12.22 mmol).
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 90℃; for 2 - 3h; A solution of dibenzofuran-4-boronic acid (1.0 g, 4.7 mmol) in ethanol (10 ML) was added to a stirred solution of 1- bromo-4-iodobenzene (1.33 g, 4.7 mmol) and tetrakis- (TRIPHENYLPHOSPHINE)-PALLADIUM (O) (271 mg, 5 molpercent) in toluene (40 mL). 2 N sodium carbonate (4.7 mL, 9.4 mmol) was added and then the reaction was heated to 90 °C (oil bath temp. ) for 2-3 h until complete (TLC control). The reaction mixture was cooled to room temperature and partitioned between water and diethyl ether. The phases were separated, the aqueous phase being further extracted with diethyl ether (2 x 20 mL). The combined organic extracts were washed with water and sat'd aq NaCl. The ethereal solution was dried over anhyd MGS04, filtered and concentrated in vacuo to yield 4- (4-BROMOPHENYL)- dibenzofuran as a yellow solid, which was used immediately without further purification. A solution of 4-formylphenylboronic acid (0.9 g, 5.64 mmol) in ethanol (10 ML) was added to a stirred solution of the crude 4- (4-BROMOPHENYL)-DIBENZOFURAN (from the previous reaction) in toluene (40 mL). TETRAKIS- (TRIPHENYLPHOSPHINE)- palladium (0) (270 mg, 5 molpercent) and 2 N sodium carbonate (4.7 mL, 9.4 mmol) were added and then the reaction was heated to 100 °C (oil bath temp. ) for 2-3 h until complete (TLC control). The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The phases were separated, the aqueous phase being further extracted with ethyl acetate (2 x 20 mL). The combined organic extracts were washed with 0.5 N hydrochloric acid, water and sat'd aq NaCl and then dried over anhyd MGS04, filtered and concentrated in vacuo. Purification by flash column chromatography (10-20percent ethyl acetate in heptane) afforded the title compound has a white solid (1.51g).

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  • 23
  • [ 110-91-8 ]
  • [ 589-87-7 ]
  • [ 30483-75-1 ]
YieldReaction ConditionsOperation in experiment
5% With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 18-crown-6 ether; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In tetrahydrofuran; at 20℃; A solution of 1-bromo-4-iodobenzene (5.0 g, 18 mmol), morpholine (1.85 mL, 21 mmol), sodium tert-butoxide (2.4 g, 25 mmol), 18-crown-6 (6.6 g, 25 mmol) in THF (150 mL)was purged with Ar for 20 min, then BINAP (0.11 g, 0.18 mmol) and Pd2(dba)3(0.16 g, 0.18 mmol) was added. The mixture turned dark after stirring at room temperature overnight. The solvent was concentrated under reduced pressure and the residue was dissolved in diethyl ether and washed with water. The organic phase was mixed with silica gel, and the solvent was evaporated to dryness. The residue was purified by silica gel column chromatography (EtOAc in hexanes 5%) to of white precipitate (250 mg, 5% yield). 1H NMR (CDCl3): 7.3 (d, 2H), 6.85 (d, 4H), 3.1 (d, 4H).
  • 24
  • [ 589-87-7 ]
  • [ 398-21-0 ]
YieldReaction ConditionsOperation in experiment
It can also be prepared in the same manner as in Preparation Example 135-(c), except for using the above Grignard reagent and 4-bromo-4'-fluorobiphenyl prepared from 4-bromo-1-iodobenzene.
  • 25
  • n-butyl lithium-hexane [ No CAS ]
  • [ 123-29-5 ]
  • [ 589-87-7 ]
  • [ 134441-71-7 ]
  • (2S,4R)-N-t-butoxycarbonyl-4-t-butyldimethylsiloxy-2-[(4-bromophenyl)hydroxymethyl]pyrrolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ammonium chloride; In tetrahydrofuran; nitrogen; ethyl acetate; REFERENCE EXAMPLE 111 (2S,4S)-4-Acetylthio-N-(p-nitrobenzyloxycarbonyl)-2-[hydroxy[4'-[(p-nitrobenzyloxycarbonylamino)methyl]-4-biphenyl]methyl]pyrrolidine diastereomer I STR315 (Step 1) A solution of 4-bromo-1-iodobenzene (9.44 g, 33.4 mmol) in tetrahydrofuran (10 ml) was added dropwise to a solution of 1.6M n-butyl lithium-hexane solution (19.0 ml, 30.3 mmol) in tetrahydrofuran (50 ml) at -78 C. for in a nitrogen stream over 15 minutes. This reaction solution was stirred -78 C. for 40 minutes and then a solution of (2S,4R)-N-t-butoxycarbonyl-4-(t-butyldimethylsiloxy)prolinal (5.0 g, 15.2 mmol) in tetrahydrofuran (17 ml) was added dropwise thereto over 10 minutes. The reaction solution was stirred at -78 C. for 1.5 hours and then saturated ammonium chloride solution was added thereto. The reaction solution was poured into a liquid mixture of ethyl acetate with water. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off in vacuo and the resulting oily residue was subjected to silica gel column chromatography (Wakogel C-300, 200 ml; ethyl acetate-heptane 2:3?3:2) to give (2S,4R)-N-t-butoxycarbonyl-4-t-butyldimethylsiloxy-2-[(4-bromophenyl)hydroxymethyl]pyrrolidine (6.30 g, yield: 85.3%) as a pale yellow oily substance. 1 H-NMR(CDCl3)delta:0.01(6H,s),0.85(9H,s),1.52(9H,s),1.76-2.08(2H,m),2.86-6.15(5H,m),7.28-7.58(4H,m)
  • 26
  • butyl lithium-hexane [ No CAS ]
  • [ 123-29-5 ]
  • [ 589-87-7 ]
  • ammonium chloride [ No CAS ]
  • [ 134441-71-7 ]
  • (2S,4R)-N-t-butoxycarbonyl-4-t-butyldimethylsiloxy-2-[(4-bromophenyl)hydroxymethyl]pyrrolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; nitrogen; ethyl acetate; REFERENCE EXAMPLE 109 (2R,4S)-4-Acetylthio-N-(p-nitrobenzyloxycarbonyl)-2-[4'-(p-nitrobenzyloxycarbonylaminomethyl)-4-biphenylmethyl]pyrrolidine STR313 (Step 1) A solution of p-bromoiodobenzene (9.44 g, 33.4 mmol) in tetrahydrofuran (10 ml) was added dropwise to a solution of 1.6M butyl lithium-hexane solution (19.0 ml, 30.3 mmol) in tetrahydrofuran (50 ml) at -78 C. in a nitrogen stream over 15 minutes. The resulting reaction solution was stirred at -78 C. for 40 minutes and then a solution of (2S,4R)-N-t-butoxycarbonyl-4-(t-butyldimethylsiloxy)prolinal (5.0 g, 15.2 mmol) in tetrahydrofuran (17 ml) was added dropwise thereto over 10 minutes. The reaction solution was stirred at -78 C. for 1.5 hours. After addition of saturated aqueous ammonium chloride, the reaction solution was poured into a liquid mixture of ethyl acetate with water. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resulting oily residue was subjected to silica gel Column chromatography (Wakogel C-300, 200 ml ethyl acetate-heptane 2:3?3:2) to give (2S,4R)-N-t-butoxycarbonyl-4-t-butyldimethylsiloxy-2-[(4-bromophenyl)hydroxymethyl]pyrrolidine (6.30 g, yield: 85.3%) as a pale yellow oily substance. 1 H-NMR(CDCl3)delta:0.01(6H,s),0.85(9H,s),1.52(9H,s),1.76-2.08(2H,m),2.86-6.15(5H,m),7.28-7.58(4H,m)
  • 27
  • [ 589-87-7 ]
  • [ 68-12-2 ]
  • [ 1032231-24-5 ]
  • 28
  • [ 589-87-7 ]
  • [ 181219-01-2 ]
  • [ 39795-60-3 ]
  • 29
  • [ 106-41-2 ]
  • [ 589-87-7 ]
  • [ 2050-47-7 ]
  • 30
  • [ 589-87-7 ]
  • [ 35578-47-3 ]
  • [ 19802-70-1 ]
YieldReaction ConditionsOperation in experiment
99% In chloroform; at 80℃; for 5h; A synthetic scheme of 2,3-bis(4-bromophenyl)quinoxaline is shown in (D-1). In a 500 mL three-necked flask were placed 30 g (82 mmol) of <strong>[35578-47-3]4,4'-dibromobenzil</strong>, 9.3 g (86 mmol) of 1,2-phenylenediamine, and 300 mL of chloroform, which were refluxed under nitrogen stream at 80 C for 5 hours. After a predetermined time, the solution was cooled to room temperature, and there was added water. The aqueous layer was extracted with chloroform, and the extract and the organic layer were dried together over magnesium sulfate. After drying, the mixture was subjected to suction filtration, and the filtrate was condensed. The obtained solid was dissolved in toluene, and the solution was subjected to suction filtration through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and alumina. The filtrate was condensed; thus, 30 g of target white powder of 2,3-bis(4-bromophenyl)quinoxaline was obtained with a yield of 99 %.
  • 31
  • [ 589-87-7 ]
  • [ 121219-08-7 ]
  • [ 63619-64-7 ]
  • 32
  • [ 2307-00-8 ]
  • [ 589-87-7 ]
  • [ 1082591-48-7 ]
  • 33
  • [ 589-87-7 ]
  • [ 223463-14-7 ]
  • [ 1206248-99-8 ]
  • 34
  • [ 589-87-7 ]
  • [ 2050-47-7 ]
  • 35
  • [ 589-87-7 ]
  • [ 220801-66-1 ]
  • [ 1338928-45-2 ]
YieldReaction ConditionsOperation in experiment
22.1% With N,N-dimethylglycine hydrochoride; caesium carbonate; copper(l) chloride; In 1,4-dioxane; for 4.0h;Inert atmosphere; Reflux; A mixture of <strong>[220801-66-1]methyl 2-(5-bromo-2-hydroxyphenyl)acetate</strong> (2.0 g, 8.16 mmol), l-bromo-4-iodobenzene (6.93 g, 24.5 mmol), 2-(dimethylamino)acetic acid hydrochloride (0.683 g, 4.90 mmol), Cs2C03 (6.65 g, 20.4 mmol) and Cu(I)Cl (0.485 g, 4.90 mmol) in dioxane (20.4 mL, 8.16 mmol) was purged with argon for 10 minutes. The mixture was then refluxed for 4 hours. HPLC showed that the reaction was complete. The mixture was then filtered through GF/F paper. The filtrate was partitioned between ethyl acetate and water. The organics were extracted with ethyl acetate twice, washed with brine and dried with Na2S04. This was then concentrated down and purified on a column using ethyl acetate and hexanes to give methyl 2-(5-bromo-2-(4-bromophenoxy)phenyl)acetate (0.721 g, 1.80 mmol, 22.1% yield).
  • 36
  • [ 201230-82-2 ]
  • [ 589-87-7 ]
  • [ 100-44-7 ]
  • [ 2001-29-8 ]
  • 37
  • [ 589-87-7 ]
  • [ 628692-15-9 ]
  • [ 27956-15-6 ]
  • 38
  • [ 589-87-7 ]
  • [ 34770-60-0 ]
  • [ 1373011-10-9 ]
  • [ 1373010-25-3 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate;trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide; In 1,4-dioxane; at 110℃; for 22h;Inert atmosphere; Sealed tube; A mixture of 1 -bromo-4-iodobenzene (0.87 g, 3.1 mmol), 4-methylpiperazin-2- one (0.30 g, 2.6 mmol), 3P04 (1.1 g, 5.1 mmol), trans-N, N'-dimethylcyclohexane-l ,2-diamine (0.08 mL, 0.51 mmol) and dioxane (5 mL) was purged with argon gas for 10 min. Copper(I) iodide (0.049 g, 0.26 mmol) was added, the vial sealed and heated at 110 C in an oil bath for 22 h. The reaction was then allowed to cool to rt and was diluted with EtOAc and saturatedNaHC03 was added. The resulting mixture was extracted with EtOAc and the combined organic extracts were dried over MgS04 and concentrated to give the crude product. Purification by silica gel chromatography (MeOH/CH2Cl2, 5:95 to 1 :9) gave an inseparable 2: 1 mixture of the desired product and l-(4-bromophenyl)-<strong>[34770-60-0]4-methylpiperazin-2-one</strong> (200 mg). NMR (400 MHz, CDCI3) 6 7.66 (d, J = 8.0 Hz, 2H), 7.02 (d, J = 8.0 Hz, 2H), 3.64 (t, J = 5.0 Hz, 2H), 3.22 (s, 2H), 2.73 (t, J = 5.0 Hz, 2H), 2.35 (s, 3H); MS ESI 317.1 [M + H]+, calcd for [C, ,H|3IN20+ H]+ 317.01.
  • 39
  • [ 244-69-9 ]
  • [ 589-87-7 ]
  • [ 694-83-7 ]
  • N-(3-bromophenyl)-γ-carboline [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; CuI; In 1,4-dioxane; ethyl acetate; 1. Synthesis of N-(3-bromophenyl)-gamma-carboline N-(3-bromophenyl)-gamma-carboline is synthesized by following Reaction Formula 8. gamma-carboline 4 g (23.8 mmol), 4-iodo-bromobenzene 8.1 g (28.5 mmol), CuI 0.58 g, 1,2-cyclohexyldiamine 0.68 g, K3PO4 12.6 g and dioxane 100 ml are put in a 250 ml two-neck flask and refluxed for 12 hours. The solution is filtered and extracted. Then, the solid is dissolved with ethylacetate, and the resulting residence is filtered by silicagel chromatography such that solid 5.0 g is obtained. (yield: 86%)
  • 40
  • [ 589-87-7 ]
  • [ 617-00-5 ]
  • [ 1373131-53-3 ]
YieldReaction ConditionsOperation in experiment
89% With potassium tert-butylate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In toluene; at 85℃; for 4h; Synthesis of Intermediate I-6 1.97 g (10.0 mmol) of Intermediate I-5, 2.83 g (10.0 mmol) of 4-bromorodobenzene, 0.18 g (0.2 mmol) of Pd2(dba)3, 0.04 g (0.4 mmol) of P(t-Bu)3, and 1.44 g (15.0 mmol) of KOtBu were dissolved in 40 ml of toluene, and the mixture was stirred at 85C for 4 hours. The mixture was cooled to room temperature and subjected to extraction three times with 30 ml of water and 30 ml of diethyl ether. An organic layer was collected and dried using magnesium sulfate to evaporate the solvent. The residue was separately purified using silica gel column chromatography to obtain 3.14 g of Intermediate I-6 (Yield: 89 %) The produced compound was identified using HR-MS. C20H18BrN Calc.: 351.0623; Measured: 351.0653
62% With tri-tert-butyl phosphine; potassium tert-butylate;tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 85℃; for 4h; 1.97g (10.0 mmol) of <strong>[617-00-5]di-ortho-tolylamine</strong>, 4.24 g (15.0 mmol) of 4-bromoiodobenzene, 0.18 g (0.2 mmol) of Pd2(dba)3, 0.04 g (0.4 mmol) of PtBu3, and 1.44 g (15.0 mmol) of KOtBu were dissolved in 40 mL of toluene to obtain a solution, which was then stirred at about 85C for about 4 hours. The reaction solution was cooled to room temperature, followed by three times of extraction with 30 mL of water and 30 mL of diethylether. The organic phase was collected, and was dried using magnesium sulfate to evaporate the solvent. The residue was separated and purified using silica gel column chromatography to obtain 2.18 g of Intermediate I-6 (Yield: 62 %). This compound was identified using LC-MS and NMR. C20H18gBrN : M+ 351.1 1H NMR (CDCl3, 400MHz) delta (ppm) 7.29-7.24 (m, 4H), 7.18-7.13 (dt, 2H), 6.92-6.84 (m, 4H), 1.96 (s, 6H)
  • 41
  • [ 589-87-7 ]
  • [ 617-00-5 ]
  • [ 1373131-54-4 ]
  • 42
  • [ 589-87-7 ]
  • [ 1257213-52-7 ]
  • [ 1380587-39-2 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; water; at 80℃; for 4.0h;Inert atmosphere; l-[4-(4,4,5,5-Tetramethyl-[l,3,2]dioxaborolan-2-yl)-phenyl]- cyclopropanecarboxylic acid ethyl ester (2 g, 6.33 mmol), l-bromo-4-iodo-benzene (1.97 g, 6.96 mmol), and sodium bicarbonate (1.59 g, 18.98 mmol) were dissolved inDME:H20 (2: 1). The solution was sparged with 2 (g) for ten minutes then (1, 1 '- bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.52 g, 0.063 mmol) was added and 2 (g) was introduced for an additional 5 minutes. The reaction was heated to 80 C for 4 hours then cooled and submitted to EtOAc/H20 workup. The crude material was purified on silica gel (0-70% EtOAc in hexanes) to provide the title compound.
  • 43
  • [ 589-87-7 ]
  • [ 2942-06-5 ]
  • [ 1418195-44-4 ]
  • 44
  • [ 859169-20-3 ]
  • [ 589-87-7 ]
  • [ 1296273-77-2 ]
YieldReaction ConditionsOperation in experiment
42% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In tetrahydrofuran; water;Inert atmosphere; Reflux; A flask was charged with compound V-9 (4 g, 13.80 mmol), compound V-10 (3.90 g, 13.80 mmol), Na2C03 (2.92 g, 27.54 mmol) and 80 mL of THF/H20 (v/v=5: l). The flask was purged with nitrogen three times, and then Pd(dppf)Cl2 (504 mg, 0.68 mmol) was added thereto. The reaction mixture was stirred at reflux overnight under nitrogen atmosphere. After being cooled to rt, the mixture was concentrated to give a residue, and it was diluted with water (50 mL), the aqueous phase was extracted with DCM (50 mL><3). The combined organic layer was washed with brine, dried over Na2S04, and concentrated. The residue was purified by column chromatography on silica gel (Petroleum ether:EtOAc = 100: 1) to afford compound V- 11 (1.80 g, yield 42%).
  • 45
  • [ 936-49-2 ]
  • [ 589-87-7 ]
  • [ 709645-78-3 ]
  • 46
  • [ 589-87-7 ]
  • [ 172732-52-4 ]
  • [ 168072-17-1 ]
  • 47
  • [ 589-87-7 ]
  • [ 172732-52-4 ]
  • [ 3096-56-8 ]
  • 48
  • [ 589-87-7 ]
  • [ 6336-32-9 ]
  • [ 1571136-18-9 ]
  • 49
  • [ 589-87-7 ]
  • [ 1049004-32-1 ]
  • [ 1620074-42-1 ]
YieldReaction ConditionsOperation in experiment
45.45% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,2-dimethoxyethane; water;Inert atmosphere; Reflux; The mixture of VI-3A (3.0 g, 10.7 mmol), VI-3 (3 g, 10.7 mmol), Na2CO3 (2.7 g, 21.4 mmol) and Pd(dppf)Cl2 in DME/H2O (90 mL, v/v=3:1) was heated to reflux under nitrogen overnight. After concentrated under reduced pressure, the mixture was partitioned between H2O (60 mL) and DCM (60 mL), the aqueous phase was extracted with DCM, and the combined organic layer was washed with brine, dried over Na2SO4, concentrated. The residue was purified by column chromatography on silica gel (PE:EA=10:1) to afford VI-4 (1.5 g, yield: 45.45%).
  • 50
  • [ 589-87-7 ]
  • [ 1049004-32-1 ]
  • [ 1620074-43-2 ]
  • 51
  • [ 589-87-7 ]
  • [ 149104-90-5 ]
  • [ 5731-01-1 ]
  • 52
  • [ 589-87-7 ]
  • [ 1765-93-1 ]
  • [ 398-21-0 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; N,N-dimethyl-formamide; at 110℃;Inert atmosphere; Sealed tube; General procedure: To a solution of 4-Methylphenylboronic acid (2.8g,21mmol) in DMF/water (v/v, 1:1) was added 1-bromo-4-iodobenzene (4g, 14mmol) , Tetrakis (triphenylphosphine)palladium (0.8g, 0.7mmol) and K2CO3 (5.8g, 42mmol), themixture was stirred at 110oC in a sealed tube under N2 over night. The reaction mixture was cooled and poured into an ice-wate rmixture solution, filtering to get solid material. The residue was purified by column chromatography on silica gel (petroleum ether) to yield the title compound
  • 53
  • [ 345954-83-8 ]
  • [ 589-87-7 ]
  • 1-(4-bromophenyl)azetidine-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
23.86% With copper(l) iodide; dimethylaminoacetic acid; caesium carbonate; In dimethyl sulfoxide; at 70℃; for 5h; To a solution of 1-bromo-4-iodobenzene (1.0 g, 3.53 mmol) in DMSO (16 mL) were added <strong>[345954-83-8]azetidine-3-carbonitrile hydrochloride</strong> (420 mg, 3.54 mmol) , cesium carbonate (1.7 g, 5.2 mmol) , N, N-dimethylglycine (400 mg, 3.80 mmol) and cuprous iodide (675 mg, 3.54 mmol) in turn. The mixture was stirred at 70 for 5 h and quenched with water (30 mL) . The resulting mixture was extracted with DCM (30 mL × 3) . The combined organic layers were dried over anhydrous Na2SO4and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with PE/EtOAc (v/v) 3/1 to give a light yellow solid product (200 mg, 23.86) .[1006]MS (ESI, pos. ion) m/z: 237.1, 238.9 [M+1]+.
  • 54
  • [ 761446-45-1 ]
  • [ 589-87-7 ]
  • 1-benzyl-4-(4-bromophenyl)pyrazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; caesium carbonate; In dimethyl sulfoxide; at 80℃; for 1h;Inert atmosphere; 4-Bromo-iodobenzene(240mg, 0.8mmol, 1.2 eq.), 1 -benzylpyrazole-4-boronic acid pinacol ester (200 mg, 0.7 mmol), potassium acetate (70 mg, 1 eq.), Pd(dppf)Cl2 (70mg, 0.1 eq.), and Cs2CO3 (700 mg, 3.0 eq.) in DMSO (5 mE) were heated under argon at 80 C. during 1 h. The reaction mixture was extracted from water into diethyl ether, dried over Na2SO4, concentrated, and chromatographed on silica gel (5-10% EtOAc/hexanes) to give 1 -benzyl-4-(4-bromophe- nyl)pyrazole (218 mg, 9 9%).11085] This bromide was converted via Methods 3 and 5 to compound 227 (142 mg, 73%). [M-Hf=277.1 mlz. Activity:A
  • 55
  • [ 589-87-7 ]
  • [ 375853-82-0 ]
  • [ 159503-91-0 ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; for 12.0h;Inert atmosphere; Reflux; Compound 21 (leq) was added compound 22 (leq), followed by potassium carbonate (3eq), [1,1 '_ bis (diphenylphosphino) ferrocene] dichloropalladium (O.leq), was added 1 , 4-dioxane: water = 4: 1, vacuum pumping, replace the nitrogen, under the protection of nitrogen reflux 12h, TLC the reaction was complete after filtration, the filter cake was washed with chloroform, the filtrate was collected, concentrated, and column chromatographed to give intermediate 23.
  • 56
  • [ 3034-53-5 ]
  • [ 589-87-7 ]
  • [ 27149-27-5 ]
YieldReaction ConditionsOperation in experiment
18.3 g A flask which in 2-bromothiazole (16.4 g) and 50 ml of THF solution were put was cooled in an iced bath, and then 55 ml of a THF solution of 2 M isopropylmagnesium chloride was added dropwise there to under in a in nitrogen atmosphere while stirring the solution. After dropewise addition the rection mixture was stirred for 1 hour, and then a zinc chloride-tetramethylethylenediamine complex (30.3 g) was added. the resuting mixture was stirring for 1 hour at room temperature, and then 1-bromo-4-iodobenzene (28.3 g) and Pd(PPh3)4 (3.5 g) were added and then heated and stirred for 1.5 hours at reflux temperature. After cooling the reaction solution to room temperature, to remove the metal ions of the catalyst, a solution prepared by dissolving the compound ethylenediamine Inc. acid, use the sodium salt dihydrate equivalent to approximately 2-fold molar with respect to the objective to the appropriate amount of water (after and it stirred to fall abbreviated) EDTA · 4Na in an aqueous solution. Then, after removing also separated by adding toluene, and the solvent was distilled off under reduced pressure to the solution, and purified by silica gel column chromatography (eluent: toluene / ethyl acetate = 50/1 (volume ratio)) to give 2-(4-bromophenyl)thiazole (18.3g).
  • 57
  • [ 864377-33-3 ]
  • [ 589-87-7 ]
  • 9-(4'-bromo-[1,1'-biphenyl]-3-yl)-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; toluene; for 10h;Inert atmosphere; Reflux; In the argon atmosphere, are respectively weighing 4-iodo-bromobenzene 28.3g (100.0mmol), 3 - (9H-carbazole-9-yl) phenyl boronic acid 30.1g (105.0mmol), Pd[PPh3]42.31g (2.00mmol), adding toluene 150 ml, dimethoxy ethane 150 ml and 2M the Na2CO3aqueous solution 150 ml (300.0mmol), heating to reflux stirring 10 hours.After the reaction, cooling to room temperature, the reaction mixture is transferred to the separatory funnel, using dichloromethane extract. The organic layer using MgSO4dried, filtered and concentrated. The concentrated residue is purified with silica gel column chromatography, to obtain 27.2g white solid (yield 68percent).
65% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 80℃; for 16h;Inert atmosphere; To a 1000 mL flask was added 30.0 g (104.5 mmol) of Intermediate 3, 38.4 g (135.8 mmol) of 1-bromo-4-iodobenzene, 36.1 g (261.2 mmol) of potassium carbonate, 6.0 g (5.2 mmol) of tetrakis (triphenylphosphine) palladium (0), 280 mL of 1,4-dioxane, After adding 140 mL of water, and the mixture was heated to 80 DEG C for 16 hours under a nitrogen stream. The resulting mixture was added to 1200 mL of methanol, and the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel / celite, an organic solvent was removed in an appropriate amount and then recrystallized from methanol to obtain Intermediate 4 (27.0 g, 65 percent Yield).
  • 58
  • [ 15854-87-2 ]
  • [ 589-87-7 ]
  • [ 39795-60-3 ]
YieldReaction ConditionsOperation in experiment
102 g 4-iodoyridine 149g and THF 689mL flown into a flask, the temperature of the contents kept 1 °C, 2.0M isopropylmagnesium chloride THF soln. 400 ml is dropwise added. after dropwise addition 15 minutes stirred, tetramethylethylenediaminezinc(II) chloride complex 202g is added, with stirring, 25 minutes at room temperature. Next, p-bromoiodobenzene 226g and tetrakis(triphenylphosphine)palladium(0) 0.34g was added and heated to reflux for 3 hours. The reaction liquid cooling to room temperature, sodium salt aqueous acetic acid ethylenediaminediacetic 4 · 4 (730g/1.7L) is added, the organic layer. After intercalating organic layer is dried by a drying agent, distilling the crude product is obtained and the solvent is reduced. This crude product is silica gel column chromatography (developing solvent: toluene-toluene/ethyl acetate = 9/1 (volume ratio)) is purified by, 4-(4-bromophenyl)pyridine 102g is obtained.
  • 60
  • [ 173194-95-1 ]
  • [ 589-87-7 ]
  • 6-(4-bromophenyl) naphthalen-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
13.5 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 3h;Inert atmosphere; Reflux; Compounds represented in the reaction vessel by the formula (I-6-1) 10.0g (0.053 mol), formula(I-6-2) with the compound represented by 15.0 g (0.053 mol), potassium carbonate 11.0 g(0.080 mol), was added tetrahydrofuran 70 mL, water 70 mL. After the inside of the system was replaced with nitrogen, was added tetrakis (triphenylphosphine) palladium (0) 0.61 g (0.53mmol). After heated to reflux for 3 h, diluted with ethyl acetate, 5% hydrochloric acid, andwashed with brine. This was purified by column chromatography (silica gel) and recrystallizationto give the formula (the I-6-3) with the compound represented by 13.5 g (0.045 mol).
  • 61
  • [ 589-87-7 ]
  • [ 55499-44-0 ]
  • C14H13Br [ No CAS ]
YieldReaction ConditionsOperation in experiment
22.8 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 5h;Inert atmosphere; Reflux; A reaction vessel The compounds of the formula (I-4-2) 15.4 g (0.103 mol), the compound represented by formula (I-4-3) 29.0g (0.103 mol), potassium carbonate 21.3g (0.154 mol) was added tetrahydrofuran 100mL, the water 100mL. Tetrakis (triphenylphosphine) palladium (0) 1.19 g (1.03 mmol) was added after the inside of the system was replaced with nitrogen, and heated to reflux for 5 hours. Diluted with toluene, washed with water, brine, and purified by column chromatography (silica gel) to give the formula (the I-4-4) with the compound represented by 22.8 g (0.0873 mol).
  • 62
  • [ 59965-20-7 ]
  • [ 589-87-7 ]
  • [ 51554-94-0 ]
  • 63
  • [ 589-87-7 ]
  • [ 90924-06-4 ]
  • 5-(4-bromophenyl)-1-methyl-1H-indole-4-carboxylic acid [ No CAS ]
  • 64
  • [ 627-12-3 ]
  • [ 589-87-7 ]
  • [ 25203-35-4 ]
YieldReaction ConditionsOperation in experiment
91% With copper(l) iodide; ethylenediamine; sodium t-butanolate; In toluene; at 100℃; for 4.0h; General procedure: CuI (10mol%) and EDA (10mol%) were added to a mixtureof O-alkyl carbamate (1mmol), NaOtBu (1.5mmol) and aryl halide (1mmol) in 2mL toluene and the mixture wasstirred for the appropriate time, which was determined byTLC monitoring, at 100C. After completion of the reaction,the catalyst was removed by filtration and 20mL H2Owas added to the filtrate. The resultant mixture was extractedwith CHCl3.Then the organic phase was washed with water(2 × 10mL) and dried over anhydrous Na2SO4.After evaporationof CHCl3under reduced pressure, the correspondingcrude product was purified by flash chromatography to givethe desired pure cross-coupling product in good to excellentyield. In the case of using arylboronic acids as couplingpartners, Cu(OAc)2 was employed instead of CuI.
  • 65
  • [ 589-87-7 ]
  • [ 151075-20-6 ]
  • C14H15BrO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; at 80℃; for 2h; To a solution of iodobromobenzene (1.1 g, 3.8 mmol) in 1,4-dioxane (10 mL) were successively added Compound 30 (1 g, 3.8 mmol), Pd(PPh3)4 (0.22 g, 0.19 mmol) and a 2 N aqueous solution of potassium carbonate (4.1 mL, 8.3 mmol), and the obtained reaction mixture was stirred at 80 C. for 2 hours. Thereafter, the reaction liquid was extracted with ethyl acetate and then drying with magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the residue was purified by silica gel column chromatography to obtain Compound 31 (0.83 g, 2.8 mmol, 75%) as a white solid. Compound 31; 1H-NMR (DMSO-d6) delta: 1.66-1.76 (m, 1H), 2.06-2.09 (m, 1H), 2.28-2.36 (m, 1H), 2.41-2.44 (m, 3H), 2.59-2.66 (m, 1H), 3.63 (s, 3H), 6.18-6.21 (m, 1H), 7.35-7.38 (m, 2H), 7.49-7.51 (m, 2H).
  • 66
  • [ 589-87-7 ]
  • [ 72232-49-6 ]
  • 1-(4-bromophenoxy)-2-chloro-3-methoxybenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
49.5% With copper(l) iodide; 3-(dimethylamino)propanoic acid hydrochloride; caesium carbonate; at 105℃; for 18h; To a solution of 1-bromo-4-iodobenzene (2 g, 7.04 mmol) in dioxane (30 ml), was added <strong>[72232-49-6]2-chloro-3-methoxyphenol</strong> (1 g, 7.04 mmol), CuI (0.134 g, 0.704 mmol), Cs2CO3 (4.59 g, 14.08 mmol), 3-(dimethylamino)propanoic acid hydrochloride (0.294 g, 0.212 mmol). The mixture was stirred at 105 C. for 18 h, the mixture was filtered, before being poured into H2O, The reaction mixture was extracted with DCM, Organic phase was purified by column chromatography on silica gel (PE) to give title product (1.2 g, yield 49.5%). 1H-NMR (400 MHz, CDCl3): delta 7.59 (d, J=8.0 Hz, 1H), 7.41 (d, J=8.0 Hz, 1H), 7.20-7.16 (m, 1H), 6.83 (d, J=8.0 Hz, 1H), 6.77 (d, J=8.0 Hz, 1H), 6.71 (d, J=8.0 Hz, 1H), 6.62 (d, J=8.0 Hz, 1H), 3.93 (s, 3H).
40.4% With copper(l) iodide; N,N-dimethylglycine hydrochoride; caesium carbonate; In 1,4-dioxane; at 105℃; for 18h;Inert atmosphere; To a solution of 1-bromo-4-iodobenzene (2.68 g, 9.5 mmol) in dioxene (40 mL) was added 3 (1.5 g, 9.5 mmol), CuT (0.182 g, 0.95 mmol), N,N-Dimethylglycine hydrochloride (0.396 g, 2.85 mmol), Cs2CO3 (6.2 g, 19 mmol). The mixture was stirred at 105C in N2 for18 h .The mixture was Filtered, contracted and extracted with EA, The organic layer was washed with water and brine, dried with anhydrous Na2504, and purified by flash chromatography to give the title product (1.2 g, 40.4 %). 1F{NMR (400 MI-Tz, CDC13): oe 7.43-7.39 (m, 2H), 7.18-7.15 (m, 1H), 6.85-6.75(m, 3H), 6.65-6.15 (m, 1H), 3.93 (s, 3H).
  • 67
  • [ 110-91-8 ]
  • [ 589-87-7 ]
  • [ 30483-75-1 ]
  • [ 4096-22-4 ]
  • 68
  • [ 589-87-7 ]
  • [ 1158098-73-7 ]
  • [ 1279089-26-7 ]
YieldReaction ConditionsOperation in experiment
40.2% To a dried 50 mL two-neck flask were added 1-bromo- 4-iodobenzene (2.10 g, 7.4 mmol) and anhydrous tetrahydrofuran (10 mL). To the mixture was added dropwise n-BuLi (3.45 mL, 2.4 mol/L) at -78C under nitrogen protection. After the addition, the mixture was stirred for 1 h, then a solution of <strong>[1158098-73-7]2-methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide</strong> (1.0 g, 5.7 mmol) in anhydrous tetrahydrofuran (8 mL) was added dropwise at -78 C. After the addition, the mixture was stirred for 0.5 h, then warmed slowly to rt and stirred overnight. After the reaction was completed, saturated aqueous ammonium chloride (3 mL) was added to quench the reaction. Then water (20 mL) and ethyl acetate (40 mL) was added to the mixture. The resulting mixture was partitioned, then the organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo, and the residue was purified by silica-gel column chromatography (n-hexane:EtOAc=1:1, V/V) to give light yellow oil (763 mg, 40.2%). MS (ESI, pos. ion) m/z: 332.1 (M+1);
To a solution of l-bromo-4-iodo-benzene (806 mg, 2.85 mmol) in anhydrous tetrahydrofuran (20 mL) was added n-BuLi (2.5 M, 1.14 mL) dropwise at -70 C and the reaction mixture was stirred for 10 min under nitrogen. Then a solution of (±)-2-methyl-N-(oxetan-3- ylidene) propane-2-sulfinamide (500 mg, 2.85 mmol, CAS 1158098-73-7) in anhydrous tetrahydrofuran (5 mL) was added dropwise and the reaction mixture was stirred at -70 C for 20 min. Then the reaction mixture was stirred at rt for 30 min. On completion, the reaction mixture was poured into 100 mL cool water and the aqueous phase was extracted with dichl orom ethane (3 X 100 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtrated and concentrated in vacuo. The resulting oil was purified by silica gel chromatography (petroleum ether: ethyl acetate = 1 : 1) to give the title compound. LCMS: (ES+) m/z (M+H)+ = 334.0, tR = 1.195. NMR (400MHz, CDCh) delta = 7.48 (d, J = 8.5 Hz, 2H), 7.23 - 7.16 (d, J = 8.5 Hz, 2H), 5.09 (d, J = 6.9 Hz, 1H), 5.01 - 4.92 (m, 2H), 4.89 - 4.83 (d, J= 6.9 Hz? 1H), 4.02 (s, 1H), 1.14 (s, 9H).
  • 69
  • [ 885693-20-9 ]
  • [ 589-87-7 ]
  • tert-butyl 3-(4-bromophenyl)-5,6-dihydropyridine-1(2H)carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 75℃; for 2h;Inert atmosphere; A mixture of tert-butyl 3 -(4,4,5,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)-5,6- dihydropyridine- 1 (2H)-carboxylate (10 g, 32.3 mmol), 1 -bromo-4-iodobenzene (9.13 g, 32.3 mmol), [1,1 ?-Bis(diphenylphosphino)ferrocene] dichloropalladium(II) (2.35 g, 3.22 mmol) and sodium carbonate (10.2 g, 96.8 mmol) in dioxane (80 mL) and water (20 mL) was purged withN2 and stirred at 75 °C for 2 h. After that, the solution was cooled to RT and purified by silica gel column chromatography (petroleum ether/ethyl acetate = 10/ito 5/1) to afford the title compound (8 g, 73percent) as a colorless oil. MS (ES+) C16H20BrNO2 requires: 337, 339, found: 282, 284 [M-55].
  • 70
  • [ 22131-92-6 ]
  • [ 589-87-7 ]
  • 3-(4-bromophenyl)thietan-3-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% To a 50 mL two-neck flask were added 4-bromoiodobenzene (0.59 g, 2.1 mmol) and anhydrous tertrahydrofuran (6 mL). Then isopropylmagnesium chloride (1.26 mL, 2.5 mmol) was added dropwise into the mixture at -40 C under nitrogen protection. The resulting mixture was stirred at -40 C for 2 h. Then a solution of thietanone (270 mg, 3.1 mmol) in tetrahydrofuran (4 mL) was added to the reaction mixture at -40 C, and the resulting mixture was warmed to rt slowly and stirred overnight. To the reaction mixture was added saturated aqueous ammonium chloride (30 mL), and the resulting mixture was extracted with ethyl acetate (30 mL*2). The combined organic layers were washed with saturated brine (20 mL*2), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo, and the residue was purified by silica-gel column chromatography (PE:DCM=1:1, V/V) to give a white solid (216 mg, 49%). MS(ESI, pos.ion)m/z:245.95 (M+2);
  • 71
  • [ 589-87-7 ]
  • [ 1376989-43-3 ]
  • [ 119233-31-7 ]
YieldReaction ConditionsOperation in experiment
6.85 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water;Inert atmosphere; 5.00 g (0.0321 mol) of the compound represented by the formula (I-3-1) was placed in a reaction vessel,9.07 g (0.0321 mol) of the compound represented by the formula (I-3-2), potassium carbonate6.65 g (0.0481 mol),50 mL of ethanol and 50 mL of water were added. After replacing the inside of the system with nitrogen, 0.37 g (0.321 mmol) of tetrakis (triphenylphosphine) palladium (0) was added. After heating and stirring, it was diluted with ethyl acetate and washed with hydrochloric acid, water and brine. Purification was carried out by column chromatography and recrystallization to obtain 6.85 g (0.0256 mol) of a compound represented by the formula (I-3-3).
  • 72
  • [ 589-87-7 ]
  • [ 20485-39-6 ]
  • ethyl 2-(4-bromophenyl)-4-methyloxazole-5-carboxylate [ No CAS ]
  • 73
  • [ 247570-24-7 ]
  • [ 589-87-7 ]
  • tert-butyl (cis-4-((4-bromophenyl)-amino)cyclohexyl)carbamate [ No CAS ]
  • 74
  • [ 86-58-8 ]
  • [ 589-87-7 ]
  • 8-(4-bromophenyl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With potassium phosphate; palladium diacetate; triphenylphosphine; In ethanol; water; toluene; at 74℃; for 15h;Inert atmosphere; Quinoline-8-boronic acid (15.16 g, 87.64 mmol), 1-iodo-4-bromobenzene (27.03 g, 95.55 mmol), acetate acetate (0.388 g, 1.73 mmol), and triphenylphosphine (1.14 g, 4.35 mmol) was charged with a 1 L round bottom flask equipped with a stir bar, a heating pack, a thermocouple, and a water condenser with a nitrogen inlet. The flask was flushed with nitrogen for 5 minutes, then degassed with toluene (360 mL), ethanol (120 mL) > and diluted with water to 120 mL, and 40 wt% potassium phosphate tribasic (115.5) g, 217.65 mmol), and added to the reaction. The reaction was heated to an internal temperature (reflux) of 74 C and stirred for 15 h. The reaction was allowed to cool to room temperature and the layers were separated. The aqueous layer was extracted with EtOAc (2×250 mL) and EtOAc evaporated. This material was purified by normal phase chromatography (methylene chloride) to give the title compound (20.03 g, 70.49 mmol, (10)%).
  • 75
  • [ 589-87-7 ]
  • [ 16292-17-4 ]
  • 76
  • [ 589-87-7 ]
  • tert-butyl(quinolin-2-yl)zinc [ No CAS ]
  • [ 24641-31-4 ]
  • 77
  • [ 892493-65-1 ]
  • [ 589-87-7 ]
  • C16H22BrNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
14% With potassium phosphate; copper(l) iodide; 2-(N,N-dimethylamino)athanol; In N,N-dimethyl-formamide; at 100℃;Inert atmosphere; Compound 60 (2 g, 7.07 mmol), Compound 167 (3.14 g, 14.1 mmol), 2-(dimethylamino) ethanol (2.34 mL, 23.3 mmol), Copper (1) iodide (135 mg, 0.707 mmol) and tripotassium phosphate (4.50 g, 21.2 mmol) was dissolved in DMF (18 ml), and the mixture was stirred at 100°C under nitrogen atmosphere. Water was added thereto, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and a saturated aqueous solution of sodium chloride, then was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain Compound 168 (340 mg, 14percent). Compound 168; Method B LC/MS retention time = 2.80 min. MS (ESI) m/z = 340.15(M+H)+.
  • 78
  • [ 589-87-7 ]
  • [ 24424-99-5 ]
  • C13H13N3O [ No CAS ]
  • [ 331834-13-0 ]
  • C22H22BrNO3 [ No CAS ]
  • 79
  • [ 589-87-7 ]
  • [ 250275-15-1 ]
  • [ 1173179-67-3 ]
YieldReaction ConditionsOperation in experiment
54% With copper(l) iodide; potassium carbonate; L-proline; In dimethyl sulfoxide; at 90℃; for 16h; General procedure: A mixture of amine GP6_1 , 4-bromo-1-iodobenzene, Cul, L-proline, K2CO3 and DMSO was stirred at 90 C for 16 h. After cooling to rt, the mixture was diluted with EtOAc. The organic phase was washed with H2O (3 *) and brine, dried over MgS04, filtered and the solvent was removed under reduced pressure. The crude could be further purified by column chromatography to afford aniline GP6_2 if necessary; tert- Butyl 5-(4-bromophenyl)hexahydropyrrolo[3,4-c]pyrrole-2(1 /-/)-carboxylate was synthesised according to general procedures GP6 - from 4-bromo-1-iodobenzene (1.39 g, 4.90 mmol), tert- butyl hexahydropyrrolo[3,4-c]pyrrole-2(1 /-/)-carboxylate (800 mg, 3.77 mmol), Cul (72.1 mg, 10%), -proline (86.8 mg, 20%), K2CO3 (67.7 mg, 4.90 mmol) and DMSO (19 ml_); 90 C, 16 h. Chromatography (EtOAc/cyclohexane 0 25%), white solid (753 mg, 54%). 1 H NMR (500 MHz, Aceton e-cfe) d 7.31 - 7.25 (m, 2H), 6.55 - 6.50 (m, 2H), 3.67 - 3.55 (m, 2H), 3.55 - 3.44 (m, 2H), 3.26 (dd, J = 1 1.4, 3.9 Hz, 2H), 3.23 - 3.14 (m, 2H), 3.11 - 3.01 (m, 2H), 1.42 (s, 9H). MS (ESI) m/z 367/369 (M+H)+
  • 80
  • [ 589-87-7 ]
  • [ 250275-15-1 ]
  • tert-butyl 5-(4-((R)-3-(benzyloxy)pyrrolidin-1-yl)phenyl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate [ No CAS ]
Same Skeleton Products
Historical Records

Similar Product of
[ 589-87-7 ]

Chemical Structure| 1261170-84-6

A1267734[ 1261170-84-6 ]

1-Bromo-4-iodobenzene-13C6

Reason: Stable Isotope