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[ CAS No. 98-80-6 ]

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2D
Chemical Structure| 98-80-6
Chemical Structure| 98-80-6
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Product Details of [ 98-80-6 ]

CAS No. :98-80-6MDL No. :MFCD00002103
Formula : C6H7BO2 Boiling Point : -
Linear Structure Formula :-InChI Key :N/A
M.W :121.93Pubchem ID :66827
Synonyms :

Computed Properties of [ 98-80-6 ]

TPSA : 40.5 H-Bond Acceptor Count : 2
XLogP3 : - H-Bond Donor Count : 2
SP3 : 0.00 Rotatable Bond Count : 1

Safety of [ 98-80-6 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P280-P305+P351+P338UN#:N/A
Hazard Statements:H302Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 98-80-6 ]

  • Upstream synthesis route of [ 98-80-6 ]
  • Downstream synthetic route of [ 98-80-6 ]

[ 98-80-6 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 98-80-6 ]
  • [ 10250-64-3 ]
YieldReaction ConditionsOperation in experiment
53% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 1 h; Inert atmosphere Step 3: Synthesis of l-methyl-3-phenyl-lH-pyrazole-5-carboxylic acid 18.3 [00343] Lithio 3 -iodo-1 -methyl- lH-pyrazole-5-carboxyl ate (18.2, 67mg, 0.26 mmol), phenylboronic acid (32mg, 0.26 mmol), K2C03 (76mg, 0.55 mmol) and Pd(PPh3)4 (30mg, 0.026 mmol) were combined in dioxane (HPLC grade, 3 ml) and water (distilled, 3ml) at rt. The mixture was purged with nitrogen for 5 minutes and then heated to 100°C (pre-heated block) with stirring. After lh the reaction was cooled down and filtered over paper washing with dioxane. The crude was loaded on silica for purification by flash column chromatography (heptane/EtOAc 100/0 to 0/100 then EtOAc/MeOH 100/0 to 30/70) to afford 29mg (53percent) of 1- methyl-3 -phenyl- lH-pyrazole-5-carboxylic acid 18.3 as a yellow glassy solid.
Reference: [1] Patent: WO2016/40449, 2016, A1, . Location in patent: Paragraph 00342-00343
  • 2
  • [ 28733-43-9 ]
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  • [ 10177-15-8 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 33, p. 5659 - 5662
[2] Journal of Organometallic Chemistry, 2003, vol. 687, # 2, p. 327 - 336
[3] Advanced Synthesis and Catalysis, 2010, vol. 352, # 18, p. 3255 - 3266
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YieldReaction ConditionsOperation in experiment
56% With pyridine; tetrakis(triphenylphosphine) palladium(0); ethanol In toluene for 20 h; Reflux (0.01 mmol, 11.5 mg) was dissolved in toluene / ethanol (V: & lt; RTI ID = 0.0 & gt; V). & Lt; / RTI & gt; A solution of 3-bromo-5- cyanopyridine (1 mmol, 0.183 g) V = 3: 1). After the reaction was allowed to proceed for 20 hours under refluxing, the reaction was stopped. The reaction mixture was allowed to stand at room temperature and washed with dichloromethane. The organic phase was collected and purified by silica gel column chromatography to give a white solid 0.11 g (yield: 56percent) of 3-phenyl-5-amidopyridine; Ms (M / Z): 198.2 (M +).
Reference: [1] Patent: CN104016914, 2016, B, . Location in patent: Paragraph 0034; 0035
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  • [ 101601-80-3 ]
YieldReaction ConditionsOperation in experiment
84% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 95℃; for 16 h; Sealed tube Example 1 1 -(trans-i -(2-methoxyethyl)-4-phenylpyrrolidin-3-yl)-3-(2-phenylpyridin-3-yl)urea1005771 Step A: Preparation of 2-phenylpyridin-3-amine: Phenyl boronic acid (92 mg,0.75 mmol), K2C03 (320 mg, 2.31 mmol) and Pd(PPh3)4 (67 mg, 0.06 mmol) were combined in toluene (3 mL), water (1.5 mL) and EtOH (0.75 mL) then treated with 2-bromopyridin-3- amine (100 mg, 0.58 mmol). The mixture was warmed to 95 °C in a sealed tube for 16 hours then cooled and partitioned between EtOAc (20 mL) and water (20 mL). The aqueous layer was extracted with EtOAc (2 x 10 mL) and the combined organic phases were washed with brine (10 mL), dried over Na2SO4, filtered and concentrated under vacuum. The residue was purified by silica column chromatography eluting with 9:1 to 4:1 hexanes/EtOAc, to afford 2- phenylpyridin-3-amine (83 mg, 84percent yield) as a pale yellow gum. MS (apci) mlz = 171.2 (M+H).
82% With potassium phosphate; tetrabutylammomium bromide In water at 85℃; for 1 h; Green chemistry General procedure: To a 10-mL reaction vial, heteroaryl halide (1.0 mmol), boronic acid (1.2 mmol), K3PO4 (2.0 mmol), tetra-butylammonium bromide (TBAB) (0.5 mmol), and 4 (0.1 mol percent) in water (3.5 mL) were added. The reaction mixture was stirred at 85 °C and the reaction progress was monitored by GC–MS analysis. After completion of the reaction, it was diluted with H2O and CH2Cl2. The organic layer was separated from mixture, the dried organic layer over MgSO4, and evaporated under reduced pressure. The crude reaction product was purified using column chromatography on silica-gel to afford the corresponding product with isolated yield up to 98percent.
Reference: [1] Patent: WO2014/78378, 2014, A1, . Location in patent: Paragraph 00577
[2] Bulletin of the Korean Chemical Society, 2016, vol. 37, # 9, p. 1478 - 1485
[3] Organic Letters, 2014, vol. 16, # 4, p. 1260 - 1263
[4] Journal of Organic Chemistry, 2016, vol. 81, # 18, p. 8520 - 8529
[5] Organic Letters, 2017, vol. 19, # 6, p. 1442 - 1445
[6] New Journal of Chemistry, 2017, vol. 41, # 24, p. 15420 - 15432
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YieldReaction ConditionsOperation in experiment
90% With sodium hydroxide; sodium carbonate; benzaldehyde In water; toluene To 2-chloro-3-aminopyridine (1.06 g, 8.24 mmol) in toluene (25 mL) was added benzaldehyde (0.878 g, 8.27 mmol).
The reaction mixture was stirred at reflux in a Dean-Stark apparatus until GC/MS analysis of the reaction mixture no longer showed starting material.
The reaction mixture was cooled to room temperature and the toluene solution containing benzylidene-(2-chloro-pyridin-3-yl)-amine was added to a mixture of phenylboronic acid (1.30 g, 10.7 mmol), sodium carbonate (2.66 g, 25.1 mmol), and tetrakis(triphenylphosphine)palladium(0) (47 mg, 0.38mol percent) in water (10 mL).
The reaction mixture was heated to 100° C. for 30 minutes, cooled to room temperature and poured into 1N aqueous sodium hydroxide (10 mL).
The aqueous layer was removed and the toluene layer was extracted with 1N aqueous hydrochloric acid (twice with 15 mL).
The aqueous layer was neutralized to pH 12 with 6N aqueous sodium hydroxide and extracted with MTBE (twice with 20 mL).
The MTBE extracts were dried over magnesium sulfate, filtered and concentrated to afford 2-phenyl-3-aminopyridine as a solid which crystallized from diisopropyl ether (1.26 g, 90percent yield). M. p.=87-68° C. 1H NMR (300 MHz, CDCl3) δ3.88 (bs, 2), 7.02-7.11 (m, 2), 7.28-7.53 (m, 3), 7.6714 7.71 (m, 2), 8.13-8.16 (m, 1).
13C NMR (100 MHz, CDCl3) δ122.57, 122.96, 128.14, 128.38, 128.72, 138.54, 139.86, 139.93, 144.93.
Reference: [1] Patent: US6316632, 2001, B1,
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YieldReaction ConditionsOperation in experiment
97% With sodium carbonate; benzaldehyde; triphenylphosphine In water; toluene A solution of palladium acetate (224.5 mg, 1.00 mmol) and triphenylphosphine (1.05 g, 4.00 mmol) in toluene (1000 mL) was stirred at room temperature for 15 minutes.
Phenylboronic acid (114 g, 935 mmol), 2-chloro-3-aminopyridine (100 g, 778 mmol), benzaldehyde (83.4 g, 786 mmol), and toluene (500 mL) were then added followed by a solution of sodium carbonate (200 g, 1.89 mol) in water (1500 mL).
The mixture was heated to reflux for 18 hours, cooled to room temperature, and the layers were separated.
The organic layer was washed with water (500 mL) and 2.5M aqueous hydrochloric acid was added (630 mL).
The aqueous layer was separated and washed with toluene (300 mL).
The pH was adjusted to 12-13 using 50percent aqueous sodium hydroxide and the mixture was extracted with methyl-tert-butyl ether (500 mL).
The organic layer was concentrated and the product was crystallized from diisopropyl ether to afford 2-phenyl-3-aminopyridine (128 g, 97percent yield). M. p.=67-68° C. 1H NMR (300 MHz, CDCl3) δ3.88 (bs, 2), 7.02-7.11 (m, 2).
7.28-7.53 (m, 3), 7.67-7.71 (m, 2), 8.,13-8.16 (m, 1).
13C NMR (100 MHz, CDCl3) δ122.57, 122.96, 128.14, 128.38, 128.72, 138.54, 139.86, 139.93, 144.93.
88% With potassium phosphate; tetrabutylammomium bromide In water at 90℃; for 6 h; Green chemistry General procedure: To a 10-mL reaction vial, heteroaryl halide (1.0 mmol), boronic acid (1.2 mmol), K3PO4 (2.0 mmol), tetra-butylammonium bromide (TBAB) (0.5 mmol), and 4 (0.1 mol percent) in water (3.5 mL) were added. The reaction mixture was stirred at 85 °C and the reaction progress was monitored by GC–MS analysis. After completion of the reaction, it was diluted with H2O and CH2Cl2. The organic layer was separated from mixture, the dried organic layer over MgSO4, and evaporated under reduced pressure. The crude reaction product was purified using column chromatography on silica-gel to afford the corresponding product with isolated yield up to 98percent.
71%
Stage #1: With bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane at 20℃; for 0.5 h; Inert atmosphere
Stage #2: With sodium carbonate In 1,4-dioxane; water at 80℃; for 8 h; Inert atmosphere
General procedure: 3-Amino-2-chloropyridine (0.5g, 3.9mmol), phenylboronic acid (0.47 g, 3.9 mmol), and bis(triphenylphosphine)palladium dichloride (0.137 g, 0.195 mmol) were added to 1,4-dioxane (20ml). Under nitrogen atmosphere the mixture was stirred at room temperature for 30 minutes. 1M aqueous sodium carbonate (8 ml) was poured in, and the temperature was raised to 80°C. After the reaction at 80°C for 8 hours, the mixture was distilled off under reduced pressure. The residue was extracted with addition of ethyl acetate and water. The impurities were filtered off from the organic layer, and the solvent was distilled off under reduced pressure. The purification by column chromatography gave the title compound (0.47 g, 71.0percent yield).
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 24, p. 9412 - 9415
[2] Patent: US6316632, 2001, B1,
[3] European Journal of Organic Chemistry, 2012, # 31, p. 6248 - 6259,12
[4] European Journal of Organic Chemistry, 2012, # 31, p. 6248 - 6259
[5] Tetrahedron Letters, 2005, vol. 46, # 20, p. 3573 - 3577
[6] Advanced Synthesis and Catalysis, 2009, vol. 351, # 17, p. 2912 - 2920
[7] Bulletin of the Korean Chemical Society, 2016, vol. 37, # 9, p. 1478 - 1485
[8] Journal of Organic Chemistry, 2005, vol. 70, # 1, p. 388 - 390
[9] Green Chemistry, 2010, vol. 12, # 11, p. 2024 - 2029
[10] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 10, p. 3010 - 3012
[11] Patent: EP2599771, 2013, A1, . Location in patent: Paragraph 0350
[12] Advanced Synthesis and Catalysis, 2013, vol. 355, # 11-12, p. 2274 - 2284
[13] New Journal of Chemistry, 2017, vol. 41, # 24, p. 15420 - 15432
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Reference: [1] Organic Process Research and Development, 2001, vol. 5, # 3, p. 254 - 256
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Reference: [1] Synthesis, 2012, vol. 2012, # 2, p. 290 - 296
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  • [ 101-23-5 ]
Reference: [1] Green Chemistry, 2018, vol. 20, # 21, p. 4891 - 4900
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  • [ 1002334-12-4 ]
Reference: [1] Patent: WO2016/615, 2016, A1,
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  • [ 1028327-66-3 ]
Reference: [1] MedChemComm, 2013, vol. 4, # 1, p. 193 - 204
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  • [ 591-50-4 ]
  • [ 1008106-86-2 ]
Reference: [1] Catalysis Communications, 2013, vol. 32, p. 15 - 17
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  • [ 1001911-63-2 ]
Reference: [1] Patent: WO2013/122402, 2013, A1,
[2] Patent: WO2013/162284, 2013, A1,
[3] Patent: WO2014/3440, 2014, A1,
[4] Patent: KR101565039, 2015, B1,
[5] Patent: KR2015/102733, 2015, A,
[6] Journal of Organometallic Chemistry, 2017, vol. 829, p. 92 - 100
[7] Polyhedron, 2014, vol. 82, p. 71 - 79
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