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[ CAS No. 53355-29-6 ]

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Chemical Structure| 53355-29-6
Chemical Structure| 53355-29-6
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CAS No. :53355-29-6 MDL No. :MFCD00439546
Formula : C13H10O4 Boiling Point : 394.7°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :230.22 g/mol Pubchem ID :2063419
Synonyms :

Safety of [ 53355-29-6 ]

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 [ 53355-29-6 ]

  • Upstream synthesis route of [ 53355-29-6 ]
  • Downstream synthetic route of [ 53355-29-6 ]

[ 53355-29-6 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 1899-24-7 ]
  • [ 99768-12-4 ]
  • [ 53355-29-6 ]
YieldReaction ConditionsOperation in experiment
81% With potassium fluoride; tri-tert-butyl phosphine In 1,4-dioxane; hexane at 65 - 70℃; for 4 h; A solution of 5-bromofuraldehyde (2.43 g, 13.9 mmoles), 4-(methoxycarbonyl)phenylboronic acid (2.50 g, 13.9 mmoles), tris(dibenzylideneacetone)palladium (0) (192 mg, 0.2 mmoles) and potassium fluoride (2.42 g, 41.7 mmoles) in 1,4-dioxane (100 ml) was added with a solution of tri-toert-butylphosphine in hexane (10percent by weight, 101 mg, 0.5 mmoles). After heating at 65-70°C for 4 hours, the mixture was cooled to room temperature and treated with methylene chloride (150 ml). After stirring for 10 minutes, the mixture was filtered through Celite and the filtrate was EPO <DP n="13"/>concentrated under reduced pressure. The residue was purified by flash silica gel chromatography eluting with an ethyl acetate-hexane mixture (1 : 1) to give 4-(5-formyl-furan-2-yl)-benzoic acid methyl ester (2.6 g, 81percent yield).1H NMR (300 MHz, CDCl3): δ 9.70 (s, IH), 8.10 (d, 2H), 7.90 (d, 2H), 7.35 (d, IH), 6.95 (d, IH), 3.98 (s, 3H).
78% With palladium diacetate; sodium carbonate In water; acetone at 20℃; for 0.416667 h; To a solution of sodium carbonate (588.2 mg, 5.55 mmol) in H2O /acetone (278 mL/ 555 mL) was added 5-bromo-2-furaldehyde (1.9 g, 11 mmol), p-(methoxycarbonyl)phenyl boronic acid (2.0 g, 11 mmol) followed by palladium acetate(24.9 mg, 0.111 mmol) in acetone (278 ml). The reaction mixture was stirred at room temperature for 25 min. The reactionwas quenched by diluting with EtOAc (855 mL) and the organic layer was washed with 1 M HCl (500 mL) twice andwith brine (500 mL) once. The organic layer was dried over Na2SO4 and filtered with silica gel, which was concentratedin vacuo. The residue was purified by flash column chromatography (CH2Cl2/hexane = 9/ 1) to give compound 9 as whitesolid (2.0 g, 8.7 mmol, 78percent)
73% With Pd(N,N-dimethyl-β-alaninate)2; sodium carbonate In ethanol; water at 120℃; for 0.166667 h; Microwave irradiation; Sealed tube General procedure: To a solution of the appropriate bromo-substituted heterocyclic aldehydes 17a (1.0 mmol) in EtOH/H2O 5:3 (tot 12 mL) in a 35 mL CEM microwave vessel, the correspondent boronic acids 18c-d (1.2 mmol), Na2CO3 2M (2.0 mmol) and Pd(N,N-Dimethyl β-alaninate)2 (5 molpercent) were added. The vessel was capped and placed in a microwave reactor and the reaction carried out with the following method in dynamic mode: 120° C, 10 min, 50W, with high stirring. After completion the vessel was allowed to cool to room temperature and the mixture was extracted with EtOAc (3 X 10 mL). The organic phase was collected, dried over anhydrous Na2SO4, and the solvent evaporated under vacuum. The crude product (containing a small portion of the ethyl ester as a transesterification product) was then purified via silica gel column chromatography (petroleum ether/EtOAc elution gradient from a 90/10 ratio to a 80/20 ratio) to obtain the pure compounds (yield 40-60percent) (Scheme 1).
Reference: [1] Patent: WO2006/66846, 2006, A1, . Location in patent: Page/Page column 11; 12
[2] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 9, p. 1562 - 1565
[3] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 63 - 70
  • 2
  • [ 27329-70-0 ]
  • [ 619-44-3 ]
  • [ 53355-29-6 ]
YieldReaction ConditionsOperation in experiment
75% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,4-dioxane; water at 100℃; Inert atmosphere General procedure: A mixture of substituted iodobenzene (2 mmol), (5-formylfuran-2-yl)boronic acid (420 mg, 3mmol, 1.5 equiv), Pd(Ph3P)2Cl2 (0.1 mmol, 0.05 equiv, 70 mg) and potassium carbonate (6 mmol,3 equiv, 828 mg) in dioxone/H2O (6 mL/2 mL) was stirred at 100 °C under argon atmosphereuntil the starting material was consumed (typically 20 h). The reaction mixture was then diluted with 25 mL of saturated brine. The mixture was then extracted with EtOAc (25 mL × 2), and the organic layers were combined, dried over Na2SO4. The concentrated crude product was purifie dby column chromatography to afford c2a-e. The second step is the same as procedure A.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 6, p. 1024 - 1029
[2] Patent: CN106977474, 2017, A, . Location in patent: Paragraph 0034; 0037; 0038
[3] Chemical Biology and Drug Design, 2018, vol. 91, # 1, p. 257 - 268
  • 3
  • [ 1899-24-7 ]
  • [ 619-44-3 ]
  • [ 53355-29-6 ]
YieldReaction ConditionsOperation in experiment
78% With potassium phosphate In N,N-dimethyl acetamide at 60℃; for 24 h; Irradiation; Green chemistry General procedure: To a solution of 1 (0.3 mmol) and 2 (0.45mmol) in DMA (5 mL) was added 3wtpercent Pd/CeO2 (80 mg). The reaction mixture was stirred under incandescent light (0.79 Wcm-2) irradiation at 60°C for 24h. After reaction (monitored by TLC), when the reaction is complete, in test tube extraction and centrifugal separation allows for isolation of the desired product, while the catalyst can be washed with ethanol and water, dried under vacuum, and reused for the next run. After completion of the reaction (monitored by TLC), water (5 mL) was added and the mixture was extracted with EtOAc (3 × 5 mL). The combined organic phase was dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by chromatography on silica gel (10:1 petroleum ether/EtOAc) to give the target product.
Reference: [1] Chinese Chemical Letters, 2018, vol. 29, # 6, p. 903 - 906
  • 4
  • [ 1899-24-7 ]
  • [ 13716-12-6 ]
  • [ 99768-12-4 ]
  • [ 53355-29-6 ]
YieldReaction ConditionsOperation in experiment
81% With potassium fluoride In hexane; dichloromethane A.
4-(5-Formyl-furan-2-yl)-benzoic Acid Methyl Ester
To a solution of 5-bromofuraldehyde (2.43 g, 13.9 mmol), 4-(methoxycarbonyl)phenyl boronic acid (2.50 g, 13.9 mmol), tris(dibenzylideneacetone)dipalladium(0) (192 mg, 0.21 mmol) and potassium fluoride (2.42 g, 41.7 mmol) in 1,4-doxane (100 ml) was added a solution of tri-t-butylphosphine in hexane (10 weight percent, 1.01 g, 0.5 mmol).
After heating at 65-70° C. for 4 hours, the mixture was cooled to room temperature and treated with dichloromethane (150 ml).
After stirring for 10 minutes, the mixture was filtered through a pad of celite and the filtrate was concentrated under reduced pressure.
The residue was purified by flash chromatography on silica gel eluding with ethyl acetate-hexane (1:1) to provide 4-(5-formyl-furan-2-yl)-benzoic acid methyl ester (2.6 g, 81percent yield).
Reference: [1] Patent: US2004/2526, 2004, A1,
  • 5
  • [ 67-56-1 ]
  • [ 39245-15-3 ]
  • [ 53355-29-6 ]
YieldReaction ConditionsOperation in experiment
85% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran (2) The prepared 4- (5-formylfuran-2-yl) benzoic acid (0.250 g, 1.16 mmol)EDCI (0.265 g, 1.39 mmol),DMAP (0.07 g, 0.058 mmol) was dissolved in 25 mL of dry tetrahydrofuran,To this was added 2 ml of anhydrous methanol,The reaction was complete by TLC detection to 4- (5-formylfuran-2-yl) benzoic acid.Rotate the solvent,The target product was obtained by silica gel column chromatography4- (5-formyl-2-furyl)Benzoate(0.227 g, white solid, 85percent)
Reference: [1] Patent: CN106565643, 2017, A, . Location in patent: Paragraph 0047; 0050
  • 6
  • [ 619-44-3 ]
  • [ 378185-02-5 ]
  • [ 53355-29-6 ]
Reference: [1] Synthesis, 2001, # 11, p. 1681 - 1685
  • 7
  • [ 2689-65-8 ]
  • [ 619-44-3 ]
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Reference: [1] Synlett, 2005, # 2, p. 267 - 270
  • 8
  • [ 27329-70-0 ]
  • [ 619-42-1 ]
  • [ 53355-29-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 17, p. 4585 - 4600
[2] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 13, p. 2159 - 2161
  • 9
  • [ 13529-27-6 ]
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Reference: [1] Synthesis, 2001, # 11, p. 1681 - 1685
  • 10
  • [ 1899-24-7 ]
  • [ 53355-29-6 ]
Reference: [1] Patent: CN106565643, 2017, A,
  • 11
  • [ 14047-29-1 ]
  • [ 53355-29-6 ]
Reference: [1] Patent: CN106565643, 2017, A,
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