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Organoboron
2-Methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine
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[ CAS No. 1609374-04-0 ] {[proInfo.proName]}

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Chemical Structure| 1609374-04-0
Chemical Structure| 1609374-04-0
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Product Details of [ 1609374-04-0 ]

CAS No. :1609374-04-0 MDL No. :MFCD32640809
Formula : C18H20BNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :FPPVNLSNFDMQGR-UHFFFAOYSA-N
M.W : 309.17 Pubchem ID :90121488
Synonyms :

Safety of [ 1609374-04-0 ]

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

Application In Synthesis of [ 1609374-04-0 ]

* 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 [ 1609374-04-0 ]

[ 1609374-04-0 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 42260-39-9 ]
  • [ 1609374-04-0 ]
  • [ 1609374-06-2 ]
YieldReaction ConditionsOperation in experiment
82% With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); XPhos; In water; ethyl acetate; toluene;Inert atmosphere; Reflux; 2-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine (5.96 g, 19.28 mmol), <strong>[42260-39-9]2-chloro-4-phenylpyridine</strong> (4.39 g, 23.13 mmol),tris(dibenzylideneacetone)palladium(0) (0.353 g, 0.386 mmol) and 2-Dicyclohexylphosphino-2?,6?-dimethoxybiphenyl (.8g, 1.951 mmol) were charged into a 500 mL 2-neck flask. Potassium phosphate tribasic (12.26 g, 57.8 mmol) was thendissolved in 45 mL of water. This solution was charged into the reaction mixture. The reaction mixture was degassedwith nitrogen then was heated to reflux overnight. The reaction mixture was cooled to room temperature. The toluenelayer was separated and was dried over magnesium sulfate. These organics were filtered and concentrated undervacuum. The crude product was passed through a silica gel column using 70-99percent toluene/ heptanes followed by 5-15percentethyl acetate/ toluene. Some of the impure product fractions were columned on silica gel using 5-15percent ethyl acetate/DCM. All the clean product fractions were combined yielding 2-methyl-8-(4-phenylpyridin-2-yl)benzofuro[2,3-b]pyridine(5.3 g, 15.76 mmol, 82 percent yield).
78% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); In water; toluene;Inert atmosphere; Reflux; A mixture of 2-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine (4.34 g, 14.03 mmol), <strong>[42260-39-9]2-chloro-4-phenylpyridine</strong> (2.66 g,14.03 mmol), Pd2(dba)3 (0.257 g 0.281 mmol), dicyclohexyl(2?,6?-dimethoxy-[1,1?-biphenyl]-2-yl)phosphine (0.582 g,1.42 mmol), potassium phosphate (8.93 g, 42.1 mmol), toluene (180 mL) and water (28 mL) was degassed with nitrogenand then refluxed overnight. The mixture was concentrated and extracted with ethyl acetate. The ethyl acetate layerwas dried on Na2SO4 and then further purified by column chromatography using ethyl acetate in hexanes to give 2-methyl-8-(4-phenylpyridin-2-yl)benzofuro[2,3-b]pyridine (3.66 g, 10.88 mmol, 78 percent yield).
Reference： [1]Patent: EP2730583,2014,A1 .Location in patent: Paragraph 0176; 0177
[2]Patent: EP2730583,2014,A1 .Location in patent: Paragraph 0231
  • 2
  • [ 886365-00-0 ]
  • [ 1609374-04-0 ]
  • 8-(5-chloro-4-methylpyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; water; at 100.0℃; for 14.0h;Inert atmosphere; 2,5-Dichloro-4-methylpyridine (7 g, 43.2 mmol), 2-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine (13.36 g, 43.2 mmol), and potassium carbonate (11.94 g, 86 mmol) were suspended in a mixture of DME (180 ml) and water (10 ml) under nitrogen at room temperature. Tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) (0.499 g, 0.432 mmol) was added as one portion, the reaction mixture was degassed and heated at 100 C. for 14 hours under nitrogen. The reaction mixture was then cooled down to room temperature and the organic phase was separated and filtered. Ethanol (100 ml) was added as one portion and the resulting mixture was stirred, then the white precipitate was filtered off. The remaining solution was evaporated and the residue was subjected to column chromatography on silica gel column, eluted with heptanes/DCM 1/1 (v/v), then heptanes/EtOAc 4/1 (v/v) to yield a white solid, which was combined with the white precipitate. The combined solids were recrystallized from DCM/heptanes, yielding 8-(5-chloro-4-methylpyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine (11 g, 83% yield).
Reference： [1]Patent: US2018/102487,2018,A1 .Location in patent: Paragraph 0125; 0126
  • 3
  • [ 1609373-98-9 ]
  • [ 73183-34-3 ]
  • [ 1609374-04-0 ]
YieldReaction ConditionsOperation in experiment
65% With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; 3 3. Synthesis of intermediate I-1 2-methylbenzofuran [2,3-b]pyridin-8-yl-trifluoromethanesulfonate (20.0 g, 60.4 mmol), bis(pinacol) diboron (16.9 g, 66.4 mmol) KOAc (17.8 g, 181.1 mmol) was dissolved in 1,4-dioxane (300 mL), and Pd(dppf)Cl2 (3 mol%), dppf (3 mol%) was added.After heating to 80 ° C and stirring overnight, the reaction mixture was cooled to room temperature.It was diluted with water and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried MgSO 4Concentrated column purification (9:1 = hexane: ethyl acetate)Intermediate I-1 (12.1 g, yield: 65%) was obtained.
63.4% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80 - 90℃; Inert atmosphere; 1.8.22-1.8.24 Step 8. Preparation of compound 8 Under the protection of N2,Add compound 7 to the reaction bottle in sequencePinacol diborate,KOAc and [1,1'-bis (diphenylphosphino) ferrocene] palladium dichloride,Soluble in 1,4-dioxane solvent,80-90 reaction for 3-5h,Then pour into ice water or saturated sodium chloride solution, extract with ethyl acetate,The organic phases are combined, washed with saturated brine, dried and spin-dried,After column separation, compound 8 is obtained. The chemical formula of compound 8 is: column separation conditions: silica gel (300-400 mesh),The eluent n-hexane: ethyl acetate = 15: 1 to 3: 1.
With potassium acetate; tricyclohexylphosphine tetrafluoroborate; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane for 24h; Reflux; 9 Intermediate Synthesis Example 9: Synthesis of Intermediate (15) In a 1-neck 500 mL flask, (2-Methylbenzofuro[2,3-b]pyridin-8-yl trifluoromethanesulfonate) 8.0 g (24.1 mol), Bis(pinacolate)diboron 7.4 g (29.0 mmol), Pd(dba)2 1.4 g (2.4 mmol), PCy3HBF41.8 g (4.8 mmol), KOAc 6.9 g (72.4 mmol) and Dioxane 120 mL were added, and the mixture was refluxed and stirred for throughout the day.After cooling to room temperature, distilled water was added to terminate the reaction, followed by extraction with DCM. After the water and solvent were completely removed, 7.0 g of the solid compound (intermediate (15)) mixed with impurities was subjected to the next reaction without any other treatment.
Reference： [1]Current Patent Assignee: ZHEJIANG HUAXIAN OPTOELECTRONICS TECHNOLOGY CO LTD - CN109810146, 2019, A Location in patent: Paragraph 0083-0085
[2]Current Patent Assignee: JIANGSU HUAYI TECHNOLOGY CO., LTD - CN110950898, 2020, A Location in patent: Paragraph 0096; 0139-0144
[3]Current Patent Assignee: LAPTO CO LTD - KR102284600, 2021, B1 Location in patent: Paragraph 0169-0171
  • 4
  • [ 109-04-6 ]
  • [ 1609374-04-0 ]
  • [ 1609373-99-0 ]
YieldReaction ConditionsOperation in experiment
80% Under the protection of nitrogen,Add intermediate I-1 (10 g, 32.3 mmol) to a three-neck bottle.2-bromopyridine (6.1 g, 38.8 mmol), 2M-potassium carbonate (80 mL)Dissolved in tetrahydrofuran (80 mL). Nitrogen replacement for 30 minutes,The catalyst tetrakistriphenylphosphine palladium (3 mol%) was added. The reaction system was warmed to 80 C and stirred under reflux for 12 hours.After cooling to room temperature, the reaction mixture was quenched with water and ethyl acetate and brine. Wash two to three times with saturated brine and take the organic phase.The organic phase was dried over anhydrous magnesium sulfate and concentrated.Separation and purification by silica gel column to obtain ligand L-2(6.7 g, yield: 80%).
Reference： [1]Patent: CN109810146,2019,A .Location in patent: Paragraph 0086-0088
  • 5
  • [ 1609373-98-9 ]
  • [ 25015-63-8 ]
  • [ 1609374-04-0 ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine In 1,2-dichloro-ethane for 18h; Inert atmosphere; Synthesis of 2-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine A solution of 2-methylbenzofuro[2,3-b]pyridin-8-yl trifluoromethanesulfonate (10 g, 30.2 mmol) and anhydrous triethylamine (20.04 ml, 151 mmol) in dichloroethane (DCE) (91 ml) was degassed with bubbling nitrogen for 15 minutes. Pd(dppf)Cl2.CH2Cl2 (1.230 g, 1.509 mmol) was added under nitrogen; then 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (13.14 ml, 91 mmol) was added via syringe and the reaction mixture was heated at 80° C. overnight. The reaction mixture was allowed to cool to room temperature then cooled in an ice/water bath. The excess 4,4,5,5-tetramethyl-1,3,2-dioxaborolane was quenched by addition of isopropanol. The crude mixture was concentrated in vacuo and used without purification in the next step
Reference： [1]Current Patent Assignee: UNIVERSAL DISPLAY CORP - US2021/399236, 2021, A1 Location in patent: Paragraph 0161-0163

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