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[ CAS No. 5467-74-3 ]

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Chemical Structure| 5467-74-3
Chemical Structure| 5467-74-3
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CAS No. :5467-74-3 MDL No. :MFCD00002104
Formula : C6H6BBrO2 Boiling Point : 315°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :200.83 g/mol Pubchem ID :79599
Synonyms :

Safety of [ 5467-74-3 ]

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:

Application In Synthesis of [ 5467-74-3 ]

  • Upstream synthesis route of [ 5467-74-3 ]
  • Downstream synthetic route of [ 5467-74-3 ]

[ 5467-74-3 ] Synthesis Path-Upstream   1~28

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  • [ 5467-74-3 ]
  • [ 22090-26-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 15, p. 3642 - 3645
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  • [ 5467-74-3 ]
  • [ 30483-75-1 ]
Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 15, p. 3642 - 3645
  • 3
  • [ 288-32-4 ]
  • [ 5467-74-3 ]
  • [ 10040-96-7 ]
YieldReaction ConditionsOperation in experiment
90% With copper(I) sulfide; N,N,N,N,-tetramethylethylenediamine In methanol at 20℃; for 24 h; General procedure: A 10mL round bottom flask was charged with a magnetic stirring bar, benzimidazole 1 (59mg, 0.5mmol), boronic acid 2 (1.0mmol), Cu2S (4mg, 0.025mmol), and MeOH (2mL), followed with the addition of TMEDA (0.075mL, 0.5mmol). The flask was sealed with a septum, through which was inserted 18-gauche needle. This setup allowed air to go into the reaction and avoid contamination of a mixture. The reaction mixture was stirred from 400 to 600rpm for appropriate time and extracted with EtOAc (2×15mL). Combined organic layers were washed with saturated aqueous solution of ethylenediaminetetraacetic acid disodium salt (15mL), and then dried over anhydrous Na2SO4. Volatiles were removed under reduced pressure and the residue was purified by column chromatography (silica gel, hexanes – EtOAc) to yield the title product, which was characterized by 1H NMR, 13C NMR, HRMS, and melting point (if solid).
81% With triethylamine In methanol at 20℃; for 5 h; General procedure: In a typical reaction, arylboronic acid (1 mmol), amino-compound (1 mmol), catalyst (5 wtpercent), Et3N (2 mmol) were mixed in methanol ( 5mL) in a 25mL round bottomed flask. The reaction mixture was subjected under continuous stirring at room temperature for 5 h. Reaction was monitored from time to time using TLC. After completion of the reaction, catalyst was separated with the aid of an external magnet and reaction mixture was taken in ethyl acetate. The organiclayer was washed using brine solution, dried over sodium sulfate. After evaporating the solvent, the crude product was puried by column chromatography using 230–400 silica mesh. The recovered catalyst was washed with methanol and ethyl acetate, dried in oven and kept in desiccator for further use.
74% With [2,2]bipyridinyl; oxygen; copper diacetate In water at 20℃; for 24 h; General procedure: Under an O2 atmosphere, a mixture of 4-methoxyphenylboroic acid (1a, 60.8 mg, 0.40 mmol), imidazole (2a, 13.6 mg, 0.20 mmol), Cu(OAc)2 (3.6 mg, 0.020 mmol), ligand I (3.7 mg, 0.020 mmol), and Brij 30 (21.8 mg, 0.060 mmol) in H2O (4 mL) was stirred at room temperature for 24 h. The mixture was diluted with brine and extracted with AcOEt (30 mL.x.3). The organic layer was washed with H2O (10 mL.x.3) and dried over MgSO4. The solvent was removed under the reduced pressure and the residue was purified by SiO2 column chromatography using AcOEt to give N-(4-methoxyphenyl)imidazole (3aa) (23.7 mg, 68percent).
Reference: [1] Synthesis, 2008, # 5, p. 795 - 799
[2] Tetrahedron, 2018, vol. 74, # 5, p. 606 - 617
[3] Green Chemistry, 2018, vol. 20, # 21, p. 4891 - 4900
[4] Catalysis Communications, 2018, vol. 109, p. 38 - 42
[5] Tetrahedron, 2012, vol. 68, # 38, p. 7794 - 7798
  • 4
  • [ 3842-55-5 ]
  • [ 5467-74-3 ]
  • [ 23449-08-3 ]
YieldReaction ConditionsOperation in experiment
96% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 12 h; Inert atmosphere Synthesis Example 32: Synthesis of Intermediate I-32 The compound, 2-chloro-4,6-diphenyl-1,3,5-triazine (50 g, 187 mmol) was dissolved in THF (1 L) under a nitrogen environment, (4-bromophenyl)boronic acid (45 g, 224.12 mmol, Aldrich Corporation), and tetrakis(triphenylphosphine)palladium (2.1 g, 1.87 mmol) were added thereto, and the mixture was stirred. Potassium carbonate saturated in water (64 g, 467 mmol) was added thereto, and the obtained mixture was heated and refluxed at 80° C. for 12 hours. When the reaction was complete, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM) and then, filtered after removing moisture with anhydrous MgSO4 and concentrated under a reduced pressure. This obtained residue was separated and purified through flash column chromatography to obtain Compound I-32 (70 g and 96percent). HRMS (70 eV, EI+): m/z calcd for C21H14BrN3: 387.0371. found: 387. Elemental Analysis: C, 65percent; H, 4percent
60% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; for 12 h; 2-chloro-4,6-diphenyl-1,3,5-triazine (20g, 1.0eq), (4- bromophenyl) boronic acid (16.5g, 1.1eq), K2CO3 (20.6g, 2.0eq), Pd (PPh3) 4 (8.6g, 0.1eq) in toluene 400 ml / 100 ml of ethanol / 50 ml H2O for 12 hours in a mixture of 100 It was stirred. And extracted with MC MC: hexane = 1: 3 to the separation column to obtain a white solid compound 72-1. (4.5g, 60percent)
60% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 53 h; Inert atmosphere The compound 2-chloro-4,6-diphenyl-1,3,5-triazine (72 g, 268 mmol) was dissolved in THF (tetrahydrofuran)(4-bromophenyl) boronic acid (45 g, 224.12 mmol) andTetrakis (triphenylphosphine) palladium (2.63 g, 2.82 mmol) was added and stirred. Saturated potassuim in waterCarbonitrile (51.6 g, 373.54 mmol), and the mixture was refluxed by heating at 80 for 53 hours. After completion of the reaction,Water was added, and the mixture was extracted with dichloromethane (DCM). Then, water was removed with anhydrous MgSO 4, filtered, and concentrated under reduced pressure. thisThe residue thus obtained was separated and purified by flash column chromatography to obtain Compound I-4 (62 g, 60percent).
30% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 60℃; for 18 h; Inert atmosphere Compound in a nitrogen stream to a flask 1L reaction [259-1] 40g (0.15mol), compound [241-6] 36.1g (0.18mol), potassium carbonateDissolve 41.4g (0.30mol) in 1,4-dioxane and 410mL, 180 mL of purified water and then put the temperature was raised to tetrakis (updated in about 60 Lee thereby phenyl phosphine) palladium added 5.2g (4.5mmol) and stirred under reflux for 18 hours. After completion of the reaction slowly to room temperature and coldSerious filtered and then the reaction solution. The filtered solid is extracted with dichloromethane, and saturated brine. The organic layer was separated, anhydrousDried with magnesium sulfate, filtered and concentrated under reduced pressure. Using the concentrate was purified by column chromatography method, to obtain the intermediate compound to prepare a [259-2] 17g (30percent).

Reference: [1] Patent: US2017/331067, 2017, A1, . Location in patent: Paragraph 0260-0263
[2] Chemistry - An Asian Journal, 2016, vol. 11, # 6, p. 868 - 873
[3] Patent: KR2015/75169, 2015, A, . Location in patent: Paragraph 0206-0209
[4] Patent: KR2015/59395, 2015, A, . Location in patent: Paragraph 0162; 0163; 0164; 0165
[5] Patent: KR2015/88163, 2015, A, . Location in patent: Paragraph 0342-0345
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  • [ 23449-08-3 ]
YieldReaction ConditionsOperation in experiment
70% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 4 h; Reflux Tetrahydrophenylphosphine palladium (2.1 g, 1.83 mmol) and potassium carbonate (75.7 g, 549 mmol) were added to a solution of p-bromophenylboronic acid (36.6 g, 183 mmol) and 2-iodo-4,6-diphenyl- 1,3,5-triazine (72.1g, 201mmol) (500mL) was degassed tetrahydrofuran,And the mixture was heated under reflux for 4 hours.The reaction mixture was cooled to room temperature,After which the solvent is removed.The residue was purified by silica gel column chromatography (49.5 g, 70percent of theory).
Reference: [1] Patent: CN106699733, 2017, A, . Location in patent: Paragraph 0054; 0055; 0056; 0057
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  • [ 2620-76-0 ]
YieldReaction ConditionsOperation in experiment
84.9% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 80℃; for 10 h; Inert atmosphere In a 250 mL three-necked flask,Access to nitrogen,0.04 mol of intermediate M1 was added,100mlTHF,0.05 mol of phenylboronic acid,0.0004 mol of tetrakis (triphenylphosphine) palladium,Stir,Then, 0.06 mol of K2CO3 aqueous solution (2 M) was added,Heated to 80 ° C,Reflux reaction for 10 hours,Sampling point plate,The reaction is complete.Natural cooling,Extracted with 200 ml of dichloromethane,The extract was dried over anhydrous sodium sulfate, filtered, the filtrate was steamed and purified on a silica gel column,Intermediate N1 was obtained, HPLC purity 99.6percent yield 84.9percent.
84.9% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 80℃; for 10 h; Inert atmosphere (2) In a 250 mL three-necked flask,Purged with nitrogen,0.04 mol of intermediate M1 was added,100mlTHF,0.05mol phenylboronic acid,0.0004 mol of tetrakis (triphenylphosphine) palladium,Stirring,Then 0.06 mol K2CO3 aqueous solution (2M) was added,Heated to 80 ° C,The reaction was refluxed for 10 hours,Sample board, the reaction was complete.The mixture was naturally cooled and extracted with 200 ml of dichloromethane. The layers were separated, the extract was dried over anhydrous sodium sulfate, filtered, and the filtrate was rotary evaporated and purified over a silica gel column to give the intermediate N1,HPLC purity 99.6percent, yield 84.9percent.
84.9% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 10 h; Inert atmosphere (2) In a 250 mL three-necked flask, purged with nitrogen, 0.04 mol of intermediate M1, 100 ml of THF, 0.05 mol of phenylboronic acid,0.0004mol tetrakis (triphenylphosphine) palladium, stirred, then add 0.06mol K2CO3 aqueous solution (2M), heated to 80 ° C, the reaction was refluxed for 10 hours, the sample point plate, the reaction was complete.The mixture was naturally cooled and extracted with 200 ml of dichloromethane. The layers were separated and the extract was dried over anhydrous sodium sulfate and filtered. The filtrate was rotary evaporated and purified on a silica gel column to give the intermediate N1 with an HPLC purity of 99.6percent and a yield of 84.9percent.
Reference: [1] Patent: CN106967052, 2017, A, . Location in patent: Paragraph 0116; 0117; 0118
[2] Patent: CN106946853, 2017, A, . Location in patent: Paragraph 0094; 0095
[3] Patent: CN107417668, 2017, A, . Location in patent: Paragraph 0123; 0124
[4] Patent: KR2015/41508, 2015, A, . Location in patent: Paragraph 0218; 0242
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  • [ 1899-24-7 ]
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  • [ 20005-42-9 ]
YieldReaction ConditionsOperation in experiment
7% With tetrabutylammomium bromide; palladium diacetate; potassium carbonate In water at 20℃; for 5 h; To a glass flask, 3 (113.8 mg, 0.650mmol), (4-bromophenyl)boronic acid (143.6 mg, 0.715 mmol), tetrabutylammonium bromide(209.6 mg, 0.650 mmol), Pd(OAc)2 (2.9 mg, 0.013 mmol) and K2CO3 (224.6 mg, 1.63 mmol)were added and then dissolved in deionized water (3 mL). The reaction mixture was stirred vigorously for 5 h at room temperature. After the white reaction mixture had become yellowand non-homogeneous, the mixture was diluted with water (10 mL), and the product was extracted with EtOAc. The organics were separated, filtered through a Celite pad, and dried with MgSO4. The organic solvent was removed under reduced pressure and the crude product was purified by dry-flash chromatography (SiO2: hexane/EtOAc = 9/1 to 7/3) to afford the title compound 5 (11 mg, 7 percent).
Reference: [1] Organic Letters, 2018, vol. 20, # 8, p. 2273 - 2277
[2] Organic Letters, 1999, vol. 1, # 7, p. 965 - 967
[3] Journal of the Serbian Chemical Society, 2017, vol. 82, # 6, p. 641 - 649
[4] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 19, p. 2681 - 2683
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  • [ 29558-77-8 ]
Reference: [1] RSC Advances, 2016, vol. 6, # 97, p. 95137 - 95148
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  • [ 29558-77-8 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 5, p. 2450 - 2461
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  • [ 2050-47-7 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 2, p. 633 - 634
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  • [ 100-44-7 ]
  • [ 2116-36-1 ]
  • [ 23450-18-2 ]
YieldReaction ConditionsOperation in experiment
63% at 100℃; for 24 h; Sealed tube To a 10 mL reaction tube containing a magnet was added (4-bromophenyl) boronic acid (201 mg, 1.0 mmol)Lithium tert-butoxide (80 mg, 1.0 mmol).Trifluorotoluene (2 mL) and benzyl chloride (63 mg, 0.5 mmol) were added.Stuffed rubber stopper,The reaction was performed on a 100 ° C electromagnetic heating stirrer for about 24 hours.After the reaction,Cool to room temperature,The organic solvent is removed using a rotary evaporator,And purified by column chromatography to give 1-benzyl-4-bromobenzeneAnd 1-benzyl-2-bromobenzene (82 mg, 63percent).The compound is a colorless oily liquid,
88.889 % de
Stage #1: Schlenk technique; Inert atmosphere
Stage #2: at 100℃; for 24 h; Schlenk technique; Inert atmosphere
General procedure: Arylboronic acid (1.0 mmol), LiOtBu (1.0 mmol) was added to a Schlenk tube. The tube was charged with nitrogen and then PhCF3 (2 mL) and benzyl chloride (0.5 mmol) were added. The reaction mixture was stirred at 100 °C for 24 h. After the mixture was cooled down to room temperature, solvent was removed under reduced pressure to leave a crude product. The crude product was purified by column chromatography on silica gel, eluting with petroleum ether to afford the coupling product.
Reference: [1] Patent: CN106478326, 2017, A, . Location in patent: Paragraph 0098; 0099; 0100; 0101; 0102
[2] Tetrahedron, 2016, vol. 72, # 49, p. 8022 - 8030
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  • [ 5467-74-3 ]
  • [ 623-33-6 ]
  • [ 14062-25-0 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10510 - 10514[2] Angew. Chem., 2014, vol. 126, # 39, p. 10678 - 10682,5
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YieldReaction ConditionsOperation in experiment
84% With sodium carbonate In toluene (1)
Synthesis of 4,4"-dibromo-p-terphenyl
Toluene 600 ml and a 2M sodium carbonate aqueous solution 300 ml were added to 1,4-diiodobenzene 33.0 g, 4-bromophenylboronic acid 48.2 g and tetrakis(triphenylphosphine)palladium (0) 4.62 g under argon atmosphere, and the mixture was refluxed for 10 hours under heating.
After finishing the reaction, the mixture was immediately filtered, and the aqueous layer was removed.
The organic layer was dried on sodium sulfate and then concentrated.
A solid matter thus obtained was recrystallized from toluene to obtain 32.6 g of white crystal of 4,4"-dibromo-p-terphenyl (yield: 84percent)
Reference: [1] Patent: WO2006/114921, 2006, A1, . Location in patent: Page/Page column 45-48
[2] Patent: US2006/232198, 2006, A1,
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  • [ 398-21-0 ]
Reference: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 2006, vol. 49, # 9, p. 817 - 827
[2] Patent: WO2012/35421, 2012, A2, . Location in patent: Page/Page column 293
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  • [ 1849-36-1 ]
  • [ 21969-12-0 ]
Reference: [1] Chemical Communications, 2016, vol. 52, # 6, p. 1170 - 1173
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  • [ 21849-89-8 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 15, p. 3962 - 3965
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  • [ 623-49-4 ]
  • [ 20201-26-7 ]
Reference: [1] Chemical Communications, 2007, # 27, p. 2855 - 2857
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  • [ 20725-34-2 ]
Reference: [1] Patent: WO2013/189865, 2013, A1,
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  • [ 75-89-8 ]
  • [ 5467-74-3 ]
  • [ 106854-77-7 ]
YieldReaction ConditionsOperation in experiment
72% With pyridine; copper diacetate; sodium carbonate In 1,2-dichloro-ethane at 20℃; for 14 h; Schlenk technique; Molecular sieve; Sealed tube General procedure: In a nitrogen-filled glove box, a 25 mL Schlenk tube equipped with a magnetic stir bar was charged with Cu(OAc)2 (9.3 mg,0.05 mmol, 0.1 equiv), aryl boronic acid 1 (0.5 mmol, 1.0 equiv),Na2CO3 (106.0 mg, 1.0 mmol, 2.0 equiv) and 4 Å MS (250.0 mg). The vessel was sealed with a septum before removing from the glovebox. The tube was evacuated and backfilled with air for 3 times.Then DCE (5.0 mL), pyridine (39.6 mg, 0.5 mmol, 1.0 equiv) and CF3CH2OH (100.0 mg, 1.0 mmol, 2.0 equiv) were added respectivelyvia syringe. The mixture was stirred vigorously under a balloon ofair at room temperature for 14 h. Then the reaction solution was vacuum-filtered over a sintered-glass funnel with a tightly packedpad of Celite (1 cm thick), and the filter cake was rinsed with DCM(20 mL). The combined filtrates were concentrated. The residue was purified with silica gel column chromatography to provide the desired product.
Reference: [1] Journal of Fluorine Chemistry, 2017, vol. 196, p. 24 - 31
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  • [ 5467-74-3 ]
  • [ 106418-67-1 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 15, p. 5313 - 5316
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  • [ 29488-24-2 ]
  • [ 5467-74-3 ]
  • [ 118621-30-0 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 38, p. 7157 - 7161
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  • [ 374564-35-9 ]
YieldReaction ConditionsOperation in experiment
87% With potassium hydrogenfluoride In methanol; water at 0℃; for 0.5 h; General procedure: To a solution of the appropriate boronic acid, 1a-j (5 mmol) in MeOH (10 mL) was added dropwise a solution of KHF2 (1.56 g, 20 mmol) in H2O (8 mL) using an addition funnel. The mixture was stirred for 30 min and concentrated under high vacuum. The residual solid was extracted with four portions of 20percent MeOH in acetone. The combined extracts were concentrated close to the saturation point and Et2O was added until no more precipitation was observed. The solid was collected, washed with two portions of Et2O, and dried under high vacuum to give the corresponding products sufficiently pure for characterization.
Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 47, p. 15792 - 15793
[2] Tetrahedron Letters, 2012, vol. 53, # 32, p. 4240 - 4242
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  • [ 374564-35-9 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 38, p. 14012 - 14015
[2] European Journal of Organic Chemistry, 2013, # 22, p. 4909 - 4917
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  • [ 1015460-59-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 15, p. 2953 - 2957
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 4778 - 4789
[3] Patent: CN106588915, 2017, A,
[4] Patent: US2018/125821, 2018, A1,
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  • [ 170230-27-0 ]
Reference: [1] Chemistry of Materials, 2016, vol. 28, # 23, p. 8556 - 8569
[2] Patent: CN105859793, 2016, A,
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  • [ 1001911-63-2 ]
Reference: [1] Patent: WO2012/39561, 2012, A1,
[2] Patent: WO2012/169821, 2012, A1,
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  • [ 1246669-45-3 ]
Reference: [1] Patent: WO2017/196081, 2017, A1,
[2] Dyes and Pigments, 2018, vol. 156, p. 369 - 378
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  • [ 5467-74-3 ]
  • [ 1191616-45-1 ]
YieldReaction ConditionsOperation in experiment
76% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,2-dimethoxyethane; water at 90℃; for 0.116667 h; Microwave irradiation; Inert atmosphere General procedure: 4-Iodo-1-methyl-1H-pyrazole 1 (101 mg, 0.5 mmol) and phenylboronic 2 (59 mg, 0.5 mmol) were dissolved in DME (3 mL) and H2O (1.2 mL) in a microwave vial under a nitrogen atmosphere. Pd(PPh3)4 (2 mmolpercent, 11.6 mg) and Cs2CO3 (407.3 mg, 1.25 mmol) were added, and the reaction mixture was irradiated in a microwave apparatus at 90 °C for 5–12 min. After the reaction mixture was cooled to ambient temperature, the product was concentrated, and the crude mixture was purified by silica gel column chromatography using petroleum ether/acetone as eluent to give the title compound.
Reference: [1] Chinese Chemical Letters, 2014, vol. 25, # 5, p. 705 - 709
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