Home Cart 0 Sign in  

[ CAS No. 1692-15-5 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1692-15-5
Chemical Structure| 1692-15-5
Structure of 1692-15-5 * Storage: {[proInfo.prStorage]}

Quality Control of [ 1692-15-5 ]

Related Doc. of [ 1692-15-5 ]

SDS
Alternatived Products of [ 1692-15-5 ]
Alternatived Products of [ 1692-15-5 ]

Product Details of [ 1692-15-5 ]

CAS No. :1692-15-5 MDL No. :MFCD01074545
Formula : C5H6BNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :122.92 g/mol Pubchem ID :2734379
Synonyms :

Safety of [ 1692-15-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1692-15-5 ]

  • Upstream synthesis route of [ 1692-15-5 ]
  • Downstream synthetic route of [ 1692-15-5 ]

[ 1692-15-5 ] Synthesis Path-Upstream   1~33

  • 1
  • [ 1692-15-5 ]
  • [ 626-64-2 ]
YieldReaction ConditionsOperation in experiment
76% With copper(ll) sulfate pentahydrate; ellagic acid In methanol at 60℃; for 8 h; Green chemistry General procedure: In a typical reaction, 10 molpercent CuSO4·5H2O, (0.049 g, 0.2 mmol)and 6.7 molpercent EA (20 mg) were mixed in methanol followed by2 mmol of phenylboronic acid. This reaction mixture was kept ina preheated oil bath by maintaining the temperature at 60 °C andstirred under atmospheric pressure. After completion of the reac-tion, modified by TLC, the mixture was washed twice with hot ethylacetate to remove the reactant and product. The hot ethyl acetatewas removed from the reaction mixture and the resulting crudeproduct was purified by a column chromatography using silicagel 260 mesh (pet ether:ethyl acetate) ratio (25:75). The recov-ered catalyst was reused for the next run. All the products werecharacterized by1H and13C NMR spectra.
Reference: [1] Journal of Molecular Catalysis A: Chemical, 2014, vol. 395, p. 500 - 505
  • 2
  • [ 1692-15-5 ]
  • [ 106-40-1 ]
  • [ 13296-04-3 ]
YieldReaction ConditionsOperation in experiment
72% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water for 3.5 h; Inert atmosphere 4-bromo-aniline 827 mg (4.81 mmol) and 4-boronic acid pyridine 519 mg (4.81 mmol. 1 eq) potassium carbonate(3.99 g 24.88 mmol 6 eq) [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (351.35 mg 481 mmol 6 eq) was placed in a 100 ml two-necked flask and infused with 30 ml (dioxane: water) =3:1) Nitrogen protection, 80 for 3.5 h. After the TLC monitoring reaction is completed, the post-treatment distillation is carried out under reduced pressure to about 10 ml, and the solution is poured into a separating funnel, extracted with dichloromethane for 2-3 times, dried over anhydrous Na 2 SO 4 , filtered, and evaporated to dryness to give a black oily drop. Separation and purification with petroleum ether: ethyl acetate = 6:1 silica gel column chromatography to obtain a pale yellow oily liquid about 590 mg, yield 72percent.
Reference: [1] Patent: CN108467370, 2018, A, . Location in patent: Paragraph 0057; 0058; 0059
[2] Journal of the American Chemical Society, 2012, vol. 134, # 9, p. 4363 - 4372
[3] Journal of Medicinal Chemistry, 2000, vol. 43, # 6, p. 1123 - 1134
  • 3
  • [ 1692-15-5 ]
  • [ 13296-04-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 22, p. 3542 - 3550
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 2474 - 2478
[3] Patent: US2013/131040, 2013, A1,
[4] Chemical Communications, 2017, vol. 53, # 95, p. 12814 - 12817
  • 4
  • [ 106-39-8 ]
  • [ 1692-15-5 ]
  • [ 5957-96-0 ]
Reference: [1] Chemistry - An Asian Journal, 2014, vol. 9, # 6, p. 1530 - 1534
  • 5
  • [ 1692-15-5 ]
  • [ 62-53-3 ]
  • [ 22961-45-1 ]
Reference: [1] Green Chemistry, 2018, vol. 20, # 21, p. 4891 - 4900
  • 6
  • [ 619-58-9 ]
  • [ 1692-15-5 ]
  • [ 4385-76-6 ]
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 27, p. 5095 - 5098
  • 7
  • [ 1120-87-2 ]
  • [ 121-43-7 ]
  • [ 7732-18-5 ]
  • [ 1692-15-5 ]
YieldReaction ConditionsOperation in experiment
65%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1 h; Inert atmosphere
Stage #2: at -78℃; for 1 h; Inert atmosphere
Stage #3: With hydrogenchloride In tetrahydrofuran at 0℃; Inert atmosphere
In the Ar gas protection,4-Bromo-pyridine (1.5 g; 10 mmol) was placed in a 200 ml Schlenk flask,After addition of 40 ml of anhydrous deoxygenated tetrahydrofuran,The reaction mixture was cooled to -78 ° C in a low temperature reactor,5 ml (2.2 M; 11 mmol) of butyllithium was added dropwise,After reaction for 1 h,4 ml of methyl borate was added,Low temperature reaction 1h and removed overnight.The reaction was quenched with 2 mol / L dilute hydrochloric acid,After recrystallization from n-hexane 0.8 g (0.8 g, 65percent yield) was obtained.
Reference: [1] Patent: CN104326980, 2016, B, . Location in patent: Paragraph 0064; 0065
  • 8
  • [ 1120-87-2 ]
  • [ 1692-15-5 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 17, p. 9258 - 9262
[2] Journal of Organic Chemistry, 2002, vol. 67, # 15, p. 5394 - 5397
[3] European Journal of Medicinal Chemistry, 2014, vol. 73, p. 167 - 176
  • 9
  • [ 19524-06-2 ]
  • [ 1692-15-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 15, p. 5661 - 5674
  • 10
  • [ 5419-55-6 ]
  • [ 19524-06-2 ]
  • [ 497-19-8 ]
  • [ 1692-15-5 ]
Reference: [1] Patent: US6174901, 2001, B1,
  • 11
  • [ 121-43-7 ]
  • [ 19524-06-2 ]
  • [ 1692-15-5 ]
Reference: [1] Inorganic Chemistry, 2001, vol. 40, # 22, p. 5536 - 5540
  • 12
  • [ 1120-87-2 ]
  • [ 5419-55-6 ]
  • [ 1692-15-5 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 8, p. 2852 - 2855
  • 13
  • [ 17249-80-8 ]
  • [ 1692-15-5 ]
  • [ 21308-82-7 ]
Reference: [1] Journal of the American Chemical Society, 2007, vol. 129, # 11, p. 3358 - 3366
  • 14
  • [ 1692-15-5 ]
  • [ 21308-82-7 ]
Reference: [1] Synlett, 2011, # 16, p. 2392 - 2396
  • 15
  • [ 24424-99-5 ]
  • [ 1692-15-5 ]
  • [ 81660-73-3 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 7, p. 1836 - 1839
  • 16
  • [ 15854-87-2 ]
  • [ 1692-15-5 ]
  • [ 1910-42-5 ]
Reference: [1] Patent: CN107935918, 2018, A,
  • 17
  • [ 154446-99-8 ]
  • [ 1692-15-5 ]
  • [ 1910-42-5 ]
Reference: [1] Patent: CN107935918, 2018, A,
  • 18
  • [ 1120-87-2 ]
  • [ 1692-15-5 ]
  • [ 1910-42-5 ]
Reference: [1] Patent: CN107935918, 2018, A,
  • 19
  • [ 619-42-1 ]
  • [ 1692-15-5 ]
  • [ 106047-17-0 ]
Reference: [1] Patent: US2008/275062, 2008, A1, . Location in patent: Page/Page column 11
  • 20
  • [ 619-44-3 ]
  • [ 1692-15-5 ]
  • [ 106047-17-0 ]
Reference: [1] Applied Organometallic Chemistry, 2019, vol. 33, # 1,
  • 21
  • [ 17763-71-2 ]
  • [ 1692-15-5 ]
  • [ 106047-17-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 13, p. 1595 - 1600
  • 22
  • [ 153034-86-7 ]
  • [ 1692-15-5 ]
  • [ 53344-73-3 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 8, p. 2852 - 2855
  • 23
  • [ 624-38-4 ]
  • [ 1692-15-5 ]
  • [ 113682-56-7 ]
  • [ 83420-59-1 ]
YieldReaction ConditionsOperation in experiment
51% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; methanol at 95℃; for 12 h; Inert atmosphere General procedure: To a solution of diiodarene 1 or 5a–c (0.306mmol) in 1,4-dioxane/MeOH (2:1, 10mL) K2CO3 (126mg, 0.918mmol) was added. The mixture was degassed by bubbling nitrogen gas through it for 15min. Pd(PPh3)4 (17mg, 0.015mmol) was added and the solution was heated to 95°C. A solution of the boronic acid (0.275mmol) in 1,4-dioxane (5mL) was added dropwise to the reaction mixture for 10h using a syringe pump. After the addition was complete, the reaction mixture was stirred at 95°C for an additional 2h. It was then allowed to cool to room temperature, the solvent was removed under reduced pressure, the residue dispersed in CH2Cl2 (10mL). This suspension was washed with water, upon which the organic phase cleared up. It was dried dried over anhydrous CaCl2, filtered and concentrated to dryness. The desired product was purified by chromatography on silica gel using 0→5percent CH2Cl2 in cyclohexane as eluent.
Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 20, p. 1948 - 1951
  • 24
  • [ 106-37-6 ]
  • [ 1692-15-5 ]
  • [ 113682-56-7 ]
Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 50, p. 14020 - 14030
[2] New Journal of Chemistry, 2018, vol. 42, # 4, p. 2526 - 2536
[3] Chemical Communications, 2015, vol. 51, # 43, p. 8998 - 9001
[4] Journal of the American Chemical Society, 2018, vol. 140, # 23, p. 7206 - 7212
[5] Chemical Communications, 2009, # 37, p. 5585 - 5587
[6] Inorganic Chemistry, 2013, vol. 52, # 8, p. 4205 - 4216
[7] Chemistry - A European Journal, 2015, vol. 21, # 45, p. 16083 - 16090
  • 25
  • [ 106-46-7 ]
  • [ 1692-15-5 ]
  • [ 113682-56-7 ]
Reference: [1] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 10, p. 3430 - 3432
  • 26
  • [ 626-05-1 ]
  • [ 1692-15-5 ]
  • [ 106047-29-4 ]
YieldReaction ConditionsOperation in experiment
74% With potassium carbonate In tetrahydrofuran; water at 80℃; for 5 h; Synthesis Example 19: Synthesis of Intermediate 16 [Show Image] 3.08 g (13 mmol) of 2,5-dibromo pyridine, 1.23 g (10 mmol) of 4-pyridyl boronic acid, 0.58 g (0.5 mmol) of Pd(PPh3)4, and 5.53 g (40 mmol) of K2CO3 were dissolved in 50 ml of a mixed solution of THF/H2O (2:1), and the mixture was stirred at 80°C for 5 hours. The mixture was subjected to extraction three times with 60 mL of diethyl ether. An organic layer was collected and dried using magnesium sulfate to evaporate the solvent. The residue was recrystallized with dichloromethane and normal hexane to obtain 1.74 g (yield: 74percent) of Intermediate 16. This compound was identified using HR-MS. C10H7BrN2 Calculated value: 233.9793; Measured value: 233.9796
72% With potassium carbonate In tetrahydrofuran; water at 80℃; for 5 h; Synthesis of Intermediate 12; 6.16 g (26 mmol) of 2,5-dibromopyridine, 2.46 g (20 mmol) of 4-pyridylboronic acid, 1.16 g (1 mmol) of Pd(PPh3)4, and 11.1 g (80 mmol) of K2CO3 were dissolved in 100 mL of a THF/H2O (2:1) mixed solution and stirred at a temperature of 80°C for 5 hours. The reaction solution was extracted three times with 100 ml of diethylether. An organic layer was collected and dried using magnesium sulfate to evaporate the solvent. The residue was re-crystallized with dichloromethane and normal hexane to obtain 3.47 g (Yield: 72percent) of Intermediate 12. The generated compound was identified using HR-MS. C10H7BrN2 calc.: 233.9793; found 233.9795
43% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 90℃; General procedure: Boronic acid or ester (10.0 mmol), K2CO3 (25.0 mmol) in H2O (10 mL) and Pd(PPh3)4 (0.3 mmol) were added sequentially to a solution of aryl halide (10.0 mmol) in 1,4-dioxane (40 mL). The reaction mixture was stirred at 90 °C for 2-20 h and was then cooled to 20 °C and partitioned between EtOAc (200 mL) and H2O (100 mL). The organic phase was washed with water (3 .x. 50 mL), washed with brine (50 mL), dried and the solvent was evaporated. The residue was purified by column chromatography, eluting with an appropriate gradient of EtOAc/pet. ether, to give the Suzuki product.
25% With potassium carbonate In 1,4-dioxane; water at 105℃; for 12 h; Reflux Synthesis of Intermediate 1d; 181.16 g (764.72 mmol) of 2,6-dibromo pyridine and 132 g (955.9 mmol) of K2CO3 were dissolved in a mixed solution of 1,4-dioxane and H2O (v/v=1000 mL:500 mL). 47 g (382.36 mmol) of pyridine-4-boronic acid, 7 g (7.65 mmol) of tris(dibenzylideneacetone)di-palladium and P(o-Tolyl)3 were added thereto and the mixture was refluxed for 12 hours while heating at 105°C. After the reaction was completed, the mixture was cooled to room temperature and washed with ethyl acetate while being filtered with Cellite. The resulting product was subjected to extraction twice using ethyl acetate by adding a NaCl solution to a water layer. The resulting product was dried using MgSO4, concentrated, filtered using column chromatography (Hex:EA=1:1), and suspension-stirred in a Hexane(30mL)-Ether(10mL) solution, and then filtered to obtain 22.5 g of Intermediate 1d (Yield: 25percent). 1H NMR (300MHz, CDCl3) δ 7.52(d, 1H), 7.66(t, 1H), 7.76(d, 1H) 7.87(d, 2H), 8.73(d, 2H).

Reference: [1] Patent: EP2289877, 2011, A1, . Location in patent: Page/Page column 21
[2] Patent: EP2292601, 2011, A1, . Location in patent: Page/Page column 23
[3] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 11, p. 3347 - 3356
[4] Patent: EP2110373, 2009, A1, . Location in patent: Page/Page column 18-19
[5] Patent: US6174901, 2001, B1,
  • 27
  • [ 76-09-5 ]
  • [ 1692-15-5 ]
  • [ 181219-01-2 ]
Reference: [1] Journal of Alloys and Compounds, 2013, vol. 555, p. 22 - 27
  • 28
  • [ 1692-15-5 ]
  • [ 126-30-7 ]
  • [ 181219-01-2 ]
Reference: [1] Journal of Fluorine Chemistry, 2009, vol. 130, # 4, p. 377 - 382
  • 29
  • [ 1692-15-5 ]
  • [ 1122-91-4 ]
  • [ 99163-12-9 ]
YieldReaction ConditionsOperation in experiment
68.4% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In tetrahydrofuran; toluene at 90℃; Inert atmosphere Compound P-formaldehyde (500 mg, 2 . 70mmol), 4-boronic acid pyridine (498.3 mg, 4 . 05mmol), double (triphenylporphyrin phosphorus) palladium dichloride Pd (PPh3)2Cl2(94.65 mg, 0 . 14mmol), dissolved in 20 ml tetrahydrofuran mixed solvent of toluene and (Vtoluene: VTHF= 1:1) in, under the protection of nitrogen 90 °C reflux reaction, thin-layer chromatography tracking to the reaction is complete. The solution obtained after the organic solvent, a revolving off, the extraction with ethyl acetate, the organic layer three times washing with water, saturated NaCl solution to a washing, drying by anhydrous sodium sulfate, reducing pressure and evaporating the solvent. The crude product using petroleum ether and ethyl acetate mixed solvent (20:1) column, to obtain 4 - (pyridin-4-yl) benzaldehyde (white solid, 288.7 mg, yield 68.4percent).
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 21, p. 6622 - 6630
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 18, p. 8402 - 8416
[3] Crystal Growth and Design, 2018, vol. 18, # 11, p. 6936 - 6945
[4] Patent: CN105418515, 2016, A, . Location in patent: Paragraph 0087; 0088; 0089
[5] Angewandte Chemie - International Edition, 2006, vol. 45, # 17, p. 2761 - 2766
[6] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 453 - 462
  • 30
  • [ 3132-99-8 ]
  • [ 1692-15-5 ]
  • [ 208190-04-9 ]
YieldReaction ConditionsOperation in experiment
30 g With palladium diacetate; sodium carbonate; triphenylphosphine In water; isopropyl alcohol at 80℃; for 48 h; Inert atmosphere Step 1Into a 2 L 3-necked round-bottom flask, purged and maintained with an inertatmosphere of nitrogen, was placed a solution of pyridin-4-ylboronic acid (30 g, 244 mmol, 1 equiv) in 2-propanol/water (800/40 mL), Na2C03 (77.3 g, 729 mmol, 3 equiv), Pd(OAc)2 (5.46 g, 24.3 mmol, 0.1 equiv), PPh3 (12.75 g, 48.7 mmol, 0.2 equiv) and 3- bromobenzaldehyde (45 g, 243 mmol, 1 equiv). The mixture was stirred for 48 h at 80°C in an oil bath. Then the solids were filtered out and the filtrate was concentrated under vacuum. The residue was purified by column chromatography on silica gel (eluting with 1 : 1 ethyl acetate/petroleum ether) to give 30 g of 3-(pyridin-4-yl)benzaldehyde as orange oil.
30 g With palladium diacetate; sodium carbonate; triphenylphosphine In water; isopropyl alcohol at 80℃; for 48 h; Inert atmosphere Into a 2 L 3-necked round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was placed a solution of pyridin-4-ylboronic acid (30 g, 244 mmol, 1 equiv) in 2-propanol/water(800/40 mL), Na2CO3 (77.3 g, 729 mmol, 3 equiv), Pd(OAc)2 (5.46 g, 24.3 mmol,0.1 equiv), PPh3 (12.75 g, 48.7 mmol, 0.2 equiv) and 3-bromobenzaldehyde (45 g, 243 mmol, 1 equiv). The mixture was stirred for 48 h at 80°C in an oil bath. Then the solids were filtered out and the filtrate was concentrated under vacuum. The residue was purified by columnchromatography on silica gel (eluting with 1:1 ethyl acetate/petroleum ether) to give 30 g of 3-(pyridin-4-yl)benzaldehyde as orange oil.
Reference: [1] Angewandte Chemie - International Edition, 2006, vol. 45, # 17, p. 2761 - 2766
[2] Patent: WO2013/16807, 2013, A1, . Location in patent: Page/Page column 23-24
[3] Patent: WO2015/127559, 2015, A1, . Location in patent: Page/Page column 31
  • 31
  • [ 1692-15-5 ]
  • [ 1032903-63-1 ]
Reference: [1] Patent: EP3150592, 2017, A1,
  • 32
  • [ 1692-15-5 ]
  • [ 1009033-87-7 ]
Reference: [1] Patent: WO2014/202528, 2014, A1,
  • 33
  • [ 1692-15-5 ]
  • [ 1045332-30-6 ]
Reference: [1] Patent: CN105601613, 2016, A,
Historical Records

Similar Product of
[ 1692-15-5 ]

Chemical Structure| 913835-65-1

A561077[ 913835-65-1 ]

Pyridin-4-ylboronic acid hydrochloride

Reason: Free-salt

Related Functional Groups of
[ 1692-15-5 ]

Organoboron

Chemical Structure| 579476-63-4

[ 579476-63-4 ]

(2-Methylpyridin-4-yl)boronic acid

Similarity: 0.86

Chemical Structure| 861905-97-7

[ 861905-97-7 ]

(2-Methylpyridin-4-yl)boronic acid hydrochloride

Similarity: 0.84

Chemical Structure| 1692-25-7

[ 1692-25-7 ]

Pyridin-3-ylboronic acid

Similarity: 0.81

Chemical Structure| 458532-94-0

[ 458532-94-0 ]

(2-Bromopyridin-4-yl)boronic acid

Similarity: 0.81

Chemical Structure| 903513-62-2

[ 903513-62-2 ]

(2-Aminopyridin-4-yl)boronic acid

Similarity: 0.81

Organoboron

Chemical Structure| 579476-63-4

[ 579476-63-4 ]

(2-Methylpyridin-4-yl)boronic acid

Similarity: 0.86

Chemical Structure| 861905-97-7

[ 861905-97-7 ]

(2-Methylpyridin-4-yl)boronic acid hydrochloride

Similarity: 0.84

Chemical Structure| 1692-25-7

[ 1692-25-7 ]

Pyridin-3-ylboronic acid

Similarity: 0.81

Chemical Structure| 458532-94-0

[ 458532-94-0 ]

(2-Bromopyridin-4-yl)boronic acid

Similarity: 0.81

Chemical Structure| 903513-62-2

[ 903513-62-2 ]

(2-Aminopyridin-4-yl)boronic acid

Similarity: 0.81

Related Parent Nucleus of
[ 1692-15-5 ]

Pyridines

Chemical Structure| 579476-63-4

[ 579476-63-4 ]

(2-Methylpyridin-4-yl)boronic acid

Similarity: 0.86

Chemical Structure| 861905-97-7

[ 861905-97-7 ]

(2-Methylpyridin-4-yl)boronic acid hydrochloride

Similarity: 0.84

Chemical Structure| 1692-25-7

[ 1692-25-7 ]

Pyridin-3-ylboronic acid

Similarity: 0.81

Chemical Structure| 458532-94-0

[ 458532-94-0 ]

(2-Bromopyridin-4-yl)boronic acid

Similarity: 0.81

Chemical Structure| 903513-62-2

[ 903513-62-2 ]

(2-Aminopyridin-4-yl)boronic acid

Similarity: 0.81