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CAS No. :5720-07-0 MDL No. :MFCD00039139
Formula : C7H9BO3 Boiling Point : 306.8°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :151.96 g/mol Pubchem ID :201262
Synonyms :

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Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
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[ 5720-07-0 ] Synthesis Path-Upstream   1~23

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Reference: [1] Patent: EP2940031, 2015, A1,
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 4, p. 989 - 994
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  • [ 5720-07-0 ]
  • [ 57677-79-9 ]
Reference: [1] Patent: WO2008/54702, 2008, A1, . Location in patent: Page/Page column 112
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  • [ 705-15-7 ]
Reference: [1] ChemPlusChem, 2017, vol. 82, # 8, p. 1129 - 1134
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  • [ 79-10-7 ]
  • [ 1929-29-9 ]
Reference: [1] Synlett, 2011, # 17, p. 2517 - 2520
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  • [ 626-02-8 ]
Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 23, p. 12154 - 12160
[2] Patent: KR101572521, 2015, B1,
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  • [ 7511-49-1 ]
Reference: [1] Patent: CN107915753, 2018, A,
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YieldReaction ConditionsOperation in experiment
95% With caesium carbonate In 1,2-dimethoxyethane; water at 80℃; for 6 h; Inert atmosphere Method B.A solution of 4-methoxyphenyl boronic acid (1 g, 6.58 mmol), 4-iodobenzoic acid (1.63 g, 6.58 mmol) and cesium carbonate (5.36 g, 16.45 mmol) in 3:1 1,2- dimethoxyethane/water was deoxygenated with nitrogen for 15 minutes. Pd(PPtLs)4 (380 mg, 0.329 mmol) was then added and the solution was heated to 80° C for 6h. The reaction was allowed to cool and acidified with 2M HCl which caused a precipitate to form. The precipitate was filtered and the filtrate was extracted twice with dichloromethane. The organic layer was then dried over magnesium sulfate, filtered through diatomaceous earth filter aid (CELITE.(R).) and evaporated under reduced pressure to yield a combined 1.5O g (95percent). 1HNMR (DMSO): δ 7.99 (d, J=8.4 Hz, 2H), 7.74 (d, J=8.4 Hz, 2H), 7.69 (d, J=8.7 Hz, 2H), 7.04 (d, J=8.7 Hz, 2H), 3.80 (s, 3H). 13CNMR (DMSO): δ 167.17, 159.49, 143.90, 131.16, 129.91, 128.77, 128.09, 126.08, 114.45, 55.17.
89% With Pd/C; potassium carbonate In water at 110℃; for 1 h; General procedure: The Ni and Pd carbon aerogels were always sinked in water 24 h before their use as catalysts and kept in the same solvent.Catalytic reactions: In a 100 mL three necked round-bottom flask, arylboronic acid (15 mmol), aryl halide (10 mmol) and K2CO3 (2.76 g, 20 mmol) were dissolved in 20 mL of H2O. Then, Ni or Pd carbon aerogel (0.1 mmol, 1 mol percent) was added to the mixture and the reaction was carried out under reflux (110 °C), in the presence of air and mechanical stirring. Periodic sampling of the reaction media was made to analyze the reaction evolution by GC and 1H NMR measurements. The liquid phase was decanted and the carbon aerogel was washed with water. This water extracts and the reactive solution were mixed together and acidified until pH 1 to cause the precipitation of the final product. The solid was filtrated, washed with water and dried. The pieces of aerogel were washed with AcOEt, with water and were kept submerged in this solvent before reused.
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[2] Green Chemistry, 2010, vol. 12, # 1, p. 150 - 158
[3] Patent: WO2009/146013, 2009, A1, . Location in patent: Page/Page column 52
[4] Green Chemistry, 2009, vol. 11, # 12, p. 1929 - 1932
[5] Tetrahedron, 2012, vol. 68, # 32, p. 6517 - 6520
[6] Green Chemistry, 2013, vol. 15, # 12, p. 3468 - 3473
[7] Tetrahedron Letters, 2006, vol. 47, # 25, p. 4225 - 4229
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YieldReaction ConditionsOperation in experiment
99% With potassium carbonate; palladium dichloride In PEG400; water at 20℃; for 0.133333 h; Air atmosphere General procedure: A mixture of arylboronic acid (0.5 mmol), aryl bromides/iodides (0.6 mmol), PdCl2 (0.0025 mmol), K2CO3 (1.75 mmol), PEG400 1.5 mL, and H2O 1.5 mL were added to a 50 mL round-flask, and stirred at room temperature for the desired time until complete consumption of starting material as judged by TLC. Then, the reaction mixture was extracted with ether (10 mL.x.4) and the combined organic layers were dried over anhydrous MgSO4 (acidification was needed for carboxyl substituted substrates before extraction). The solvent was removed by evaporation under reduced pressure to afford the crude products, which were further purified by column chromatography on silica gel using petroleum ether and ethyl acetate as the eluent.
Reference: [1] Tetrahedron, 2011, vol. 67, # 26, p. 4914 - 4918
[2] Asian Journal of Chemistry, 2014, vol. 26, # 7, p. 2077 - 2082
[3] Organic and Biomolecular Chemistry, 2014, vol. 12, # 25, p. 4511 - 4516
[4] Applied Organometallic Chemistry, 2014, vol. 28, # 12, p. 861 - 867
[5] Green Chemistry, 2010, vol. 12, # 1, p. 150 - 158
[6] Journal of the American Chemical Society, 2009, vol. 131, # 23, p. 8262 - 8270
[7] Green Chemistry, 2009, vol. 11, # 12, p. 1929 - 1932
[8] Journal of Medicinal Chemistry, 1997, vol. 40, # 20, p. 3144 - 3150
[9] Tetrahedron Letters, 2004, vol. 45, # 29, p. 5661 - 5663
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Reference: [1] Synthesis (Germany), 2013, vol. 45, # 9, p. 1201 - 1206
[2] RSC Advances, 2017, vol. 7, # 74, p. 47104 - 47110
[3] Organic and Biomolecular Chemistry, 2014, vol. 12, # 25, p. 4511 - 4516
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Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 11, p. 4189 - 4194
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Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 34, p. 13308 - 13310
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Reference: [1] Journal of Organometallic Chemistry, 2007, vol. 692, # 20, p. 4244 - 4250
[2] Journal of Organometallic Chemistry, 2007, vol. 692, # 20, p. 4244 - 4250
[3] Journal of Organometallic Chemistry, 2007, vol. 692, # 20, p. 4244 - 4250
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Reference: [1] Journal of Organometallic Chemistry, 2007, vol. 692, # 20, p. 4244 - 4250
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Reference: [1] ChemCatChem, 2016, vol. 8, # 23, p. 3626 - 3635
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Reference: [1] Organic Letters, 2006, vol. 8, # 9, p. 1787 - 1789
[2] Journal of Organic Chemistry, 2007, vol. 72, # 14, p. 5104 - 5112
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Reference: [1] Synlett, 2012, vol. 23, # 9, p. 1305 - 1308
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Reference: [1] Patent: CN104788483, 2017, B, . Location in patent: Paragraph 0022; 0023; 0024
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YieldReaction ConditionsOperation in experiment
68% With palladium diacetate; sodium carbonate; triphenylphosphine In tetrahydrofuran; water at 60℃; for 6 h; [00234] To a solution of 2,4,6-trichloropyrimidine (5.5 mL, 48 mmol) in THF (70 mL) were added palladium acetate (0.147 g, 0.64 mmol), triphenylphosphine (0.353 g, 1.28 mmol), 4-methoxybenzeneboronic acid (5 g, 31.9 mmol) and aqueous sodium carbonate solution (1 M, 64 mL, 64 mmol). The mixture was stirred at 60 °C for 6 h. After the reaction was completed, the mixture was cooled to rt, and concentrated in vacuo to remove the solvent. To the residue was added H20 (100 mL), and the mixture was extracted with ethyl acetate (100 mL x 3). The combined organic layers were washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (PE) to give the title compound as a white solid (5.58 g, 68percent).MS (ESI, pos.ion) m/z: 255.0 [M+H]+1H NMR (400 MHz, CDC13) (ppm): 8.07 (dd, J = 9.4, 2.4 Hz, 2H), 7.60 (s, 1H), 7.08-6.99 (m,2H), 3.91 (s, 3H).
68% With palladium diacetate; sodium carbonate; triphenylphosphine In tetrahydrofuran; water at 60℃; To a solution of 2,4,6-trichloropyrimidine (5.5 mL, 48.0 mmol) in tetrahydrofuran (70 mL) were added palladium acetate (0.147 g, 0.64 mmol), triphenylphosphine (353 mg, 1.28 mmol), 4-methoxyphenylboronic acid (5 g, 31.9 mmol) and an aqueous sodium carbonate soltuion (1 M, 64 mL, 64 mmol). The mixture was heated to 60 °C and stirred overnight. After the reaction, the reaction mixture was cooled to rt and concentrated to remove the organic solvent. To the residue was added H20 (100 mL), and the mixture was extracted with EtOAc (100 mL x 3). The combined organic layers were washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuoto dry,and the residue was purified by silica gel column chromatography (PE) to give the title compound as a white solid (5.58 g, 68percent).MS (ESI, pos.ion) m/z: 255.0 [M+Hfb;‘H NIVIR (400 IVIFIz, CDC13) (ppm): 8.07 (dd, J = 9.4, 2.4 Hz, 2H), 7.60 (s, 1H), 7.08 — 6.99 (m, 2H), 3.91 (s, 3H).
68% With palladium diacetate; sodium carbonate; triphenylphosphine In tetrahydrofuran; water at 60℃; for 6 h; Inert atmosphere 2,4,6-Trichloropyrimidine (5.5 mL, 48.0 mmol) was dissolved in tetrahydrofuran (70 mL).Then, palladium acetate (0.147 g, 0.64 mmol) was sequentially added thereto.Triphenylphosphine (353 mg, 1.28 mmol),p-Methoxybenzeneboronic acid (5.01 g, 31.9 mmol)And aqueous sodium carbonate (1M, 64 mL, 64 mmol),The resulting mixture was heated to 60 ° C under a nitrogen atmosphere and stirred for 6 hours.Cool to room temperature, concentrate under reduced pressure to remove organic solvent.Water (100 mL) was added to the residue.The resulting mixture was extracted with ethyl acetate (100 mL×3).The combined organic phases were washed with brine (100 mL).Dry anhydrous sodium sulfate, filter, and concentrate the filtrate to dryness.The residue was purified by EtOAc EtOAc EtOAc(5.58g, 68percent).
68% With palladium diacetate; sodium carbonate; triphenylphosphine In tetrahydrofuran; water at 60℃; for 6 h; Inert atmosphere To a solution of 2,4,6-trichloropyrimidine (5.5 mL, 48.0 mmol) in THF (70 mL) were added palladium acetate (0.147 g, 0.64 mmol), triphenylphosphine (353 mg, 1.28 mmol), 4-methoxybenzeneboronic acid (5.01 g, 31.9 mmol) and aqueous sodium carbonate solution (1 M, 64 mL, 64 mmol). The mixture was stirred at 60 °C for 6 h under nitrogen protection. The reaction mixture was cooled to rt and concentrated in vacuo to remove the solvent. To the residue was added water (100 mL), and the resulting mixture was extracted with ethyl acetate (100 mL x3). The combined organic layers were washed with saturated brine (100 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (PE) to give the title compound as a white solid (5.58 g, 68percent). MS (ESI, pos.ion) m/z: 255.0 [M+H]‘H NMR (400 IVIFIz, CDC13) (ppm): 8.07 (dd, J= 9.4, 2.4 Hz, 2H), 7.60 (s, 1H), 7.08 — 6.99 (m, 2H), 3.91 (s, 3H).
68% With palladium diacetate; sodium carbonate; triphenylphosphine In tetrahydrofuran; water at 60℃; for 5 h; To a solution of 2, 4, 6-trichloropyrimidine (5.5 mL, 48.0 mmol) in THF (70 mL) were added palladium acetate (0.147 g, 0.64 mmol) , triphenylphosphine (353 mg, 1.28 mmol) , p-methoxybenzeneboronic acid (5 g, 31.9 mmol) and aqueous sodium carbonate solution (1 M, 64 mL, 64 mmol) . The mixture was stirred at 60 for 5 h. The reaction mixture was cooled to rt and concentrated in vacuo to remove organic solvent. To the residue was added water (100 mL) , and the resulting mixture was extracted with ethyl acetate (100 mL × 3) . The combined organic layers were washed with saturated brine (100 mL) , dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (PE) to give the title compound as a white solid (5.58 g, 68percent) .[0757]MS-ESI: (ESI, pos. ion) m/z: 255.0 [M+H]+;[0758]1H NMR (400 MHz, CDCl3) δ (ppm) : 8.07 (dd, J = 9.4, 2.4 Hz, 2H) , 7.60 (s, 1H) , 7.08–6.99 (m, 2H) , 3.91 (s, 3H) .

Reference: [1] Organic Letters, 2006, vol. 8, # 3, p. 395 - 398
[2] Patent: WO2017/97234, 2017, A1, . Location in patent: Paragraph 00234
[3] Patent: WO2018/33082, 2018, A1, . Location in patent: Paragraph 00441
[4] Patent: CN108276401, 2018, A, . Location in patent: Paragraph 0595; 0597; 0598
[5] Patent: WO2018/127096, 2018, A1, . Location in patent: Paragraph 00284
[6] Patent: WO2018/157830, 2018, A1, . Location in patent: Paragraph 00298
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Reference: [1] Patent: EP2308838, 2011, A1,
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Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 50, p. 15284 - 15288[2] Angew. Chem., 2015, vol. 127, # 50, p. 15499 - 15503,5
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Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 22, p. 11513 - 11524
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