27329-70-0

Usage

Uses

Used in Chemical Synthesis:
2-Formylfuran-5-boronic acid is used as a bifunctional reagent for the synthesis of π-extended heteroarylfuran systems. Its unique structure allows for the formation of complex molecular structures with potential applications in various industries.
Used in Suzuki Reaction:
In the field of organic chemistry, 2-Formylfuran-5-boronic acid is used as a reactant in Suzuki coupling, a widely employed method for the formation of carbon-carbon bonds. This reaction is particularly useful for the synthesis of stable dye-sensitized solar cells, contributing to the development of renewable energy technologies.
Used in Pharmaceutical Industry:
2-Formylfuran-5-boronic acid is used as a reactant in the synthesis of biologically active molecules. It plays a crucial role in the development of various pharmaceutical compounds, such as:
HIF-1 inhibitors: These molecules are involved in the regulation of cellular responses to hypoxia and have potential applications in the treatment of cancer and other diseases.
Disalicylic acid-furanyl derivatives: These compounds are designed to inhibit ephrin binding, which can be useful in the development of drugs targeting various signaling pathways.
HIV-1 integrase inhibitors: These molecules are essential in the development of antiretroviral drugs, as they help prevent the integration of the HIV virus into the host genome.
Epidermal growth factor receptor inhibitors: These compounds are used in the treatment of various cancers by targeting the epidermal growth factor receptor, a key player in cell proliferation and survival.

InChI:InChI=1/C5H5BO4/c7-3-4-1-2-5(10-4)6(8)9/h1-3,8-9H

Synthetic route

2-(diethoxymethyl)furan (13529-27-6) + Trimethyl borate (121-43-7) → 5-formylfurane-2-boronic acid (27329-70-0)

Conditions	Yield
Stage #1: 2-(diethoxymethyl)furan With biphenyl; para-chlorotoluene; lithium In tetrahydrofuran at -65℃; for 9h; Stage #2: Trimethyl borate In tetrahydrofuran at -65℃; for 1h; Stage #3: With hydrogenchloride In tetrahydrofuran; water pH=6.3;	81.5%
With n-butyllithium In tetrahydrofuran; hexane soln. of n-BuLi in hexane added dropwise to soln. of the acetal in THF at -78°C, stirred at -78°C for 5 h, dropwise addn. of trimethylborate, allowed to warm to 25°C with stirring overnight; aqueous workup, org. solvent removed under vac., aq. NaOH added to aq. phase (pH 10), washed with ether, aq. phase acidified carefully with 48% HBr (pH 4), ppt. filtered off, washed with ether; elem. anal.;	52%

5-bromo-2-furancarboxaldehyde (1899-24-7) + Triisopropyl borate (5419-55-6) → 5-formylfurane-2-boronic acid (27329-70-0)

Conditions	Yield
Stage #1: 5-bromo-2-furancarboxaldehyde With n-butyllithium In tetrahydrofuran; hexane; toluene at -60 - -50℃; for 1.16667h; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane; toluene	78%

2-(diethoxymethyl)furan (13529-27-6) → 5-formylfurane-2-boronic acid (27329-70-0)

Conditions	Yield
Stage #1: 2-(diethoxymethyl)furan With Triisopropyl borate; lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -10 - 0℃; for 1h; Stage #2: With hydrogenchloride In tetrahydrofuran; n-heptane; ethylbenzene; water at 30℃;	75%
Stage #1: 2-(diethoxymethyl)furan With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 5h; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -78 - 25℃; Stage #3: With sodium hydroxide pH=10; Further stages.;	52%

2-(furan-2-yl)-1,3-dioxolane (1708-41-4) → 5-formylfurane-2-boronic acid (27329-70-0)

Conditions	Yield
Stage #1: 2-(furan-2-yl)-1,3-dioxolane With biphenyl; Trimethyl borate; lithium; isoprene In tetrahydrofuran at 22 - 25℃; for 3.5h; Stage #2: With hydrogenchloride In tetrahydrofuran; water Product distribution / selectivity;
Stage #1: 2-(furan-2-yl)-1,3-dioxolane With Trimethyl borate; lithium; isoprene In tetrahydrofuran at 25 - 30℃; for 4.16667h; Stage #2: With hydrogenchloride In tetrahydrofuran; water Product distribution / selectivity;
Stage #1: 2-(furan-2-yl)-1,3-dioxolane With biphenyl; lithium; isoprene In tetrahydrofuran; toluene at 23 - 26℃; for 1.66667h; Stage #2: In tetrahydrofuran; water; toluene Product distribution / selectivity; Acidic conditions;
Stage #1: 2-(furan-2-yl)-1,3-dioxolane With biphenyl; Triisopropyl borate; sodium In tetrahydrofuran at 5 - 25℃; for 3.25h; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 0℃; Product distribution / selectivity;

Triisopropyl borate (5419-55-6) + C10H12O4Zn → 5-formylfurane-2-boronic acid (27329-70-0)

Conditions	Yield
With copper(I) iodide-lithium chloride In tetrahydrofuran at 20℃; Schlenk technique; Inert atmosphere;

5-formylfurane-2-boronic acid (27329-70-0) + o-nitroiodobenzene (609-73-4) → 5-(2-nitrophenyl)-2-furaldehyde (20000-96-8)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 50℃; for 3h; Suzuki reaction;	100%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 80℃; for 3h; Suzuki Coupling;

(3S)-4-[7-chloro-2-[(3S)-3-methylmorpholin-4-yl]pyrido[2,3-d] pyrimidin-4-yl] 3-methyl-morpholine (1009303-44-9) + 5-formylfurane-2-boronic acid (27329-70-0) → C22H25N5O4

Conditions	Yield
With potassium phosphate; bis(tri-t-butylphosphine)palladium(0) In 1,4-dioxane at 170℃; for 0.75h; Microwave radiation;	100%

5-formylfurane-2-boronic acid (27329-70-0) + ethyl 3-bromo-4-cyanobenzoate (362527-61-5) → ethyl 4-cyano-3-(5-formyl-2-furyl)benzoate

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In tetrahydrofuran; water at 50℃; for 18h; Suzuki-Miyaura Coupling;	100%

5-formylfurane-2-boronic acid (27329-70-0) + methyl 5-iodosalicylate (4068-75-1) → 5-(5-formylfuran-2-yl)-2-hydroxybenzoic acid (330977-65-6)

Conditions	Yield
With potassium carbonate In ethanol; water for 24h; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube; Heating;	100%

5-formylfurane-2-boronic acid (27329-70-0) + N-(4-([1,2,4]triazolo[4,3-c]pyrimidin-7-yloxy)-3-methylphenyl)-6-iodoquinazolin-4-amine → 5-(4-((4-([1,2,4]triazolo[4,3-c]pyrimidin-7-yloxy)-3-methylphenyl)amino)quinazolin-6-yl)furan-2-carbaldehyde

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine In tetrahydrofuran for 16h; Reflux;	99.9%

5-formylfurane-2-boronic acid (27329-70-0) + para-iodoanisole (696-62-8) → 5-(4-methoxyphenyl)furan-2-carbaldehyde (34070-33-2)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 50℃; for 1h; Suzuki reaction;	99%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 80℃; for 3h; Suzuki Coupling;
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 60℃; for 1h; Suzuki Coupling;

3-Bromopyridine (626-55-1) + 5-formylfurane-2-boronic acid (27329-70-0) → 5-(pyridin-3-yl)-furan-2-carbaldehyde (38588-49-7)

Conditions	Yield
With PdCl2-[5-(1,1'-biphenyl-4-yl)isoxazole-3-carbaldehyde oxime]; potassium carbonate In methanol; water at 100℃; for 0.0833333h; Suzuki Coupling;	99%
With bis-triphenylphosphine-palladium(II) chloride; tetrabutylammomium bromide; potassium carbonate In chloroform; water at 80 - 100℃; for 0.166667h;	98%
With tetrabutylammomium bromide; potassium carbonate In methanol; water at 80℃; for 0.333333h; Suzuki Coupling; Reflux;	96%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 12h; Suzuki cross-coupling; Heating;

5-formylfurane-2-boronic acid (27329-70-0) + methyl 4-iodosalicylate (18179-39-0) → methyl 4-(5-formylfuran-2-yl)-2-hydroxybenzoate (1277116-14-9)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In ethanol; N,N-dimethyl-formamide at 20℃; Suzuki coupling; Inert atmosphere;	99%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In ethanol; N,N-dimethyl-formamide at 20℃; for 1h; Suzuki Coupling; Inert atmosphere;	96%
Stage #1: 5-formylfurane-2-boronic acid; methyl 4-iodosalicylate In ethanol; N,N-dimethyl-formamide for 0.166667h; Suzuki Coupling; Inert atmosphere; Stage #2: With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In ethanol; N,N-dimethyl-formamide at 20℃; for 1h; Suzuki Coupling; Inert atmosphere;	96%
Stage #1: 5-formylfurane-2-boronic acid; methyl 4-iodosalicylate In ethanol; N,N-dimethyl-formamide for 0.166667h; Suzuki Coupling; Inert atmosphere; Stage #2: With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In ethanol; N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	96%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In ethanol; N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	64%

5-formylfurane-2-boronic acid (27329-70-0) + N-{3-chloro-4-[(2-fluorobenzyl)oxy]phenyl}-6-iodoquinazoline-4-amine hydrochloride (1393112-43-0) → 5-[4-({3-chloro-4-[(2-fluorobenzyl)oxy]phenyl}amino)quinazoline-6-yl]furan-2-carbaldehyde (1393112-44-1)

Conditions	Yield
With potassium carbonate; palladium diacetate In tetrahydrofuran; ethanol at 75℃; for 1h; Inert atmosphere;	98.8%
With palladium diacetate; potassium carbonate In tetrahydrofuran; ethanol at 75℃; for 1h; Inert atmosphere;	98.8%

5-formylfurane-2-boronic acid (27329-70-0) + N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-iodoquinazolin-4-amine (231278-20-9) → 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde (231278-84-5)

Conditions	Yield
With potassium carbonate; palladium diacetate In tetrahydrofuran; ethanol for 0.666667h; Product distribution / selectivity; Reflux;	98.7%
With palladium; triethylamine In tetrahydrofuran; ethanol at 65℃; for 7h; Temperature; Concentration; Inert atmosphere;	97.7%
With triethylamine; palladium 10% on activated carbon In methanol; 1,2-dimethoxyethane at 45 - 50℃; for 15h; Suzuki Coupling; Inert atmosphere;	96%

5-formylfurane-2-boronic acid (27329-70-0) + 5-iodoanthranilonitrile (132131-24-9) → 2-amino-5-[(5-formyl)furan-2-yl]benzonitrile

Conditions	Yield
With palladium 10% on activated carbon; triethylamine In methanol; 1,2-dimethoxyethane at 20 - 45℃; for 3h; Suzuki Coupling;	98.6%

6-iodo-N-(3-methyl-4-((6-methylpyridin-3-yl)oxy)phenyl)quinazolin-4-amine (537705-05-8) + 5-formylfurane-2-boronic acid (27329-70-0) → 5-(4-(4-(6-methylpyridin-3-yloxy)-3-methylphenylamino)quinazolin-6-yl)furan-2-carbaldehyde (1260402-39-8)

Conditions	Yield
With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,2-dimethoxyethane; ethanol at 75℃; for 4h; Inert atmosphere;	98%
With bis-triphenylphosphine-palladium(II) chloride; triethylamine In methanol for 12h; Suzuki Coupling; Reflux;

5-formylfurane-2-boronic acid (27329-70-0) + 4-iodobenzoic acid ethyl ester (51934-41-9) → 5-(4-ethoxycarbonylphenyl)furan-2-carbaldehyde (19247-87-1)

Conditions	Yield
With potassium carbonate In ethanol; water at 20℃; for 0.5h; Suzuki-Miyaura Coupling; Sealed tube; Green chemistry;	98%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 60℃; for 1h;	73.8%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 60℃; for 1h; Suzuki Coupling;

5-formylfurane-2-boronic acid (27329-70-0) + 1-Fluoro-3-iodobenzene (1121-86-4) → 5-(3'-fluorophenyl)furan-2-carbaldehyde (33342-18-6)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 65℃; for 1h; Suzuki Coupling;	98%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 80℃; for 3h; Suzuki Coupling;

6-iodoquinazolin-4(3H)-one (16064-08-7) + 5-formylfurane-2-boronic acid (27329-70-0) → 5-(4-oxo-3,4-dihydroquinazolin-6-yl)furan-2-carbaldehyde (1334953-71-7)

Conditions	Yield
Stage #1: 5-formylfurane-2-boronic acid With palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate In water; dimethyl sulfoxide at 20℃; for 0.333333h; Inert atmosphere; Stage #2: 6-iodoquinazolin-4(3H)-one With potassium acetate In water; dimethyl sulfoxide at 75 - 85℃; for 0.333333h; Inert atmosphere;	97.6%
With tri tert-butylphosphoniumtetrafluoroborate; palladium diacetate In water; dimethyl sulfoxide at 20 - 80℃; Product distribution / selectivity; Inert atmosphere;	97.6 %Chromat.

5-formylfurane-2-boronic acid (27329-70-0) + 1-iodo-4-((trifluoromethyl)sulfonyl)benzene (360-01-0) → 5-[4-(trifluoromethanesulfonyl)phenyl]-2-furaldehyde

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 50℃; for 1h; Suzuki reaction;	97%

5-iodo-1,2,3-trimethoxybenzene (25245-29-8) + 5-formylfurane-2-boronic acid (27329-70-0) → 5-(3,4,5-trimethoxyphenyl)furan-2-carbaldehyde (62427-26-3)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 65℃; for 1h; Suzuki Coupling;	97%

5-formylfurane-2-boronic acid (27329-70-0) + chlorobenzene (108-90-7) → 5-phenylfuran-2-carbaldehyde (13803-39-9)

Conditions	Yield
With potassium phosphate; C75H58Cl2N4Pd In water; isopropyl alcohol at 25℃; for 24h; Reagent/catalyst; Suzuki-Miyaura Coupling; Schlenk technique;	97%

5-formylfurane-2-boronic acid (27329-70-0) + 4-bromo-7-(11-butyl-11H-benzo[a]carbazol-5-yl)benzo[c][1,2,5]- thiadiazole → 5-(7-(11-butyl-11H-benzo[a]carbazol-5-yl)benzo[c][1,2,5]- thiadiazol-4-yl)furan-2-carbaldehyde

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 10h; Suzuki Coupling; Reflux;	97%

5-formylfurane-2-boronic acid (27329-70-0) + 4-Iodobenzotrifluoride (455-13-0) → 5-(4-(trifluoromethyl)phenyl)furan-2-carbaldehyde (55377-77-0)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile	96.15%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 60℃; for 1h; Suzuki Coupling;

5-formylfurane-2-boronic acid (27329-70-0) + m-bromobenzoic acid (585-76-2) → 5-(3-carboxyphenyl)furane-2-carbaldehyde (304884-54-6)

Conditions	Yield
With C11H8Cl4N2O3Pd; potassium carbonate In methanol; water; N,N-dimethyl-formamide at 100℃; for 0.166667h; Suzuki Coupling;	96%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 12h; Suzuki cross-coupling; Heating;
With 2-[5-(4-methylphenyl)isoxazol-3-yl]-5-(5-phenylisoxazol-3-yl)-1,3,4-oxadiazole·2PdCl2; potassium carbonate In methanol; water; N,N-dimethyl-formamide at 20℃; for 0.416667h; Suzuki Coupling;	0.21 g

5-formylfurane-2-boronic acid (27329-70-0) + toluene-4-sulfonic acid (104-15-4) + 5-iodoanthranilonitrile (132131-24-9) → 2-amino-5-[(5-formyl)furan-2-yl]benzonitrile p-toluenesulfonic acid

Conditions	Yield
Stage #1: 5-formylfurane-2-boronic acid; 5-iodoanthranilonitrile With palladium 10% on activated carbon; triethylamine In methanol; 1,2-dimethoxyethane at 20 - 45℃; for 3h; Stage #2: toluene-4-sulfonic acid In water at 60℃;	96%

5-formylfurane-2-boronic acid (27329-70-0) + 2-bromo-9-[4-(diphenylamino)phenyl]-5,12-dioctylquinolino[2,3-b]acridine-7,14-dione (1352543-77-1) → 5-{9-[4-(diphenylamino)phenyl]-5,12-dioctyl-7,14-dioxo-5,7,12,14-tetrahydroquinolino[2,3-b]acridin-2-yl}furan-2-carbaldehyde (1352543-79-3)

Conditions	Yield
Stage #1: 2-bromo-9-[4-(diphenylamino)phenyl]-5,12-dioctylquinolino[2,3-b]acridine-7,14-dione With tetrakis(triphenylphosphine) palladium(0); water; potassium carbonate In tetrahydrofuran for 0.5h; Suzuki Coupling; Reflux; Stage #2: 5-formylfurane-2-boronic acid In tetrahydrofuran for 12h; Suzuki Coupling; Reflux;	95.4%

1-Chloro-4-iodobenzene (637-87-6) + 5-formylfurane-2-boronic acid (27329-70-0) → 5-(4-chlorophenyl)-2-furaldehyde (34035-03-5)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 65℃; for 1h; Suzuki Coupling;	95%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 80℃; for 3h; Suzuki Coupling;

5-formylfurane-2-boronic acid (27329-70-0) + methyl 5-bromo-4-methoxy-2-methylbenzoate → methyl 5-(5-formyl-2-furyl)-4-methoxy-2-methylbenzoate

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In tetrahydrofuran; water at 50℃; for 18h; Suzuki-Miyaura Coupling;	95%

N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-iodoquinazolin-4-amine hydrochloride (851684-46-3) + 5-formylfurane-2-boronic acid (27329-70-0) → 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde (231278-84-5)

Conditions	Yield
With triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In ethanol for 2h; Heating / reflux;	94%

2-chloropyridine (109-09-1) + 5-formylfurane-2-boronic acid (27329-70-0) → 5-(pyridin-2-yl)furan-2-carboxaldehyde (55484-36-1)

Conditions	Yield
With potassium carbonate; sodium tetrachloropalladate(II) In water; butan-1-ol at 100℃; for 12h; Suzuki cross-coupling;	94%

5-formylfurane-2-boronic acid (27329-70-0) + C20H15FINO3 (1351125-09-1) → C25H18FNO5 (1351125-22-8)

Conditions	Yield
With palladium diacetate; potassium hydroxide In water; acetone at 35℃; Suzuki coupling;	94%

3-Chloropyridine (626-60-8) + 5-formylfurane-2-boronic acid (27329-70-0) → 5-(pyridin-3-yl)-furan-2-carbaldehyde (38588-49-7)

Conditions

Yield

Stage #1: 3-Chloropyridine; 5-formylfurane-2-boronic acid With palladium diacetate; (R)-6-dicyclohexylphoshino-6'-diphenylphosphino-3,3'-dimethoxy-2,2',4,4'-tetramethyl-1,1'-biphenyl In dodecane; butan-1-ol at 25℃; for 16h; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox; Stage #2: With cesiumhydroxide monohydrate In dodecane; water; butan-1-ol at 25℃; Suzuki-Miyaura Coupling; Glovebox; Inert atmosphere;

94%

2-thienyl chloride (96-43-5) + 5-formylfurane-2-boronic acid (27329-70-0) → 5-(thiophen-2-yl)furan-2-carboxaldehyde (32364-30-0)

Conditions

Yield

Stage #1: 2-thienyl chloride; 5-formylfurane-2-boronic acid With palladium diacetate; (R)-6-dicyclohexylphoshino-6'-diphenylphosphino-3,3'-dimethoxy-2,2',4,4'-tetramethyl-1,1'-biphenyl In dodecane; butan-1-ol at 25℃; for 1h; Suzuki-Miyaura Coupling; Glovebox; Inert atmosphere; Stage #2: With cesiumhydroxide monohydrate In dodecane; water; butan-1-ol at 80℃; for 4h; Suzuki-Miyaura Coupling; Glovebox; Inert atmosphere;

94%

Upstream product

• 13529-27-6 2-(diethoxymethyl)furan 
• 121-43-7 Trimethyl borate 
• 5419-55-6 Triisopropyl borate 
• 1899-24-7 5-bromo-2-furancarboxaldehyde 
• 1708-41-4 2-(furan-2-yl)-1,3-dioxolane 

Downstream Products

• 13803-39-9 5-phenylfuran-2-carbaldehyde 
• 32364-30-0 5-(thiophen-2-yl)furan-2-carboxaldehyde 
• 577975-32-7 5-(5-cyanopyridin-3-yl)-furan-2-carbaldehyde 
• 13130-10-4 5-(4-hydroxyphenyl)-2-furancarboxaldehyde 
• 34070-33-2 5-(4-methoxyphenyl)furan-2-carbaldehyde 
• 52130-32-2 5-[4-cyanophenyl]-2-furancarboxaldehyde 
• 20000-96-8 5-(2-nitrophenyl)-2-furaldehyde 
• 53355-29-6 4-(5-formyl-2-furanyl)benzoic acid methyl ester 
• 33342-17-5 5-(4'-fluorophenyl)furan-2-carbaldehyde 
• 765937-67-5 5-(4-trifluoromethylsulfanylphenyl)furan-2-carbaldehyde 
• 38588-49-7 5-(pyridin-3-yl)-furan-2-carbaldehyde 
• 380566-25-6 5-(2'-fluorophenyl)furan-2-carbaldehyde 
• 55377-84-9 5-(3-methoxyphenyl)furan-2-carbaldehyde 
• 900515-32-4 5-(2-benzyloxy-4-fluorophenyl)furan-2-carbaldehyde 

Relevant academic research and scientific papers

Copper-Catalyzed Monoorganylation of Trialkyl Borates with Functionalized Organozinc Pivalates

Organozinc pivalates, a recently developed air- and moisture-stable organozinc species, were found for the first time as excellent organometallic species in the monoorganylation of trialkyl borates whereby boronic acids were prepared in high yields. The significant advantage of organozinc pivalates over another previously employed organometallic reagents, e. g., organolithium reagents, Grignard reagents and organozinc halides, is that the generation of multiorganylation byproducts such as borinic acids and trialkylboranes were completely suppressed. Additionally, the in situ generated boronates could be directly arranged into Suzuki-Miyaura type cross-coupling reactions to produce biaryls in high yields.

Discovery of selective protein arginine methyltransferase 5 inhibitors and biological evaluations

Protein arginine methyltransferase 5 (PRMT5) is an important protein arginine methyltransferase that catalyzes the symmetric dimethylation of arginine resides on histones or non-histone substrate proteins. It has been thought as a promising target for many diseases, particularly cancer. Despite the potential applications of PRMT5 inhibitors in cancer treatment, very few of PRMT5i have been publicly reported. In this investigation, virtual screening and structure–activity relationship studies were carried out to discover novel PRMT5i, which finally led to the identification of a number of new PRMT5i. The most active compound, P5i-6, exhibited a considerable inhibitory potency against PRMT5 with an IC50 value of 0.57?μm, and a high selectivity for PRMT5 against other tested PRMTs. It displayed a very good antiviability activity against two colorectal cancer cell lines, HT-29 and DLD-1, and one hepatic cancer cell line, HepG2, in a sensitivity assay against 36 different cancer cell lines. Western blot assays indicated that P5i-6 selectively inhibited the symmetric dimethylations of H4R3 and H3R8 in DLD-1 cells. Overall, P5i-6 could be used as a chemical probe to investigate new functions of PRMT5 in biology and also served as a good lead compound for the development of new PRMT5-targeting therapeutic agents.

METHODS FOR DETECTING AND REDUCING IMPURITIES OF LAPATINIB AND SALTS THEREOF

Impurities of lapatinib such as N-{3-chloro-4-[(2-fluorobenzyl)oxy]phenyl}-6-[5-({[2-(methylsulfonyl)ethyl]amino}methyl)furan-2-yl]quinazoline-4-amine compound of formula (I) or a salt thereof: and analytical methods for identifying and quantifying such impurities of Lapatinib and salts thereof are provided. Also provided is Lapatinib containing less than about 0.05 percent of this and related impurities and methods for preparing such pure forms of Lapatinib.

Method for the Production of Functionalized Five-Ring Heterocycles, and use thereof

A method for producing functionalized CH-acidic five-ring heterocycles, the resultant five-ring heterocycles and the use thereof for producing pharmaceuticals and crop protection preparations.

METHOD FOR METAL-ORGANIC PRODUCTION OF ORGANIC INTERMEDIATE PRODUCTS BY MEANS OF ARYL LITHIUM-BASES

The invention relates to a method for the production of substituted aromatic compounds by producing lithium arylene and by reacting it with suitable electrophiles. The method comprises the following steps (step 1); an aryl lithium compound ( auxiliary base'') is initially produced by reacting a halogen aromatic compound with lithium metal; said compound is subsequently (step 2) reacted for deprotonation of the aromatic substrate in order to form the corresponding lithium aromatic compound which is subsequently (step 3) reacted with a corresponding electrophile to form the desired substituted aromatic compound, see page 2 of the description.

Method of producing 5-formyl-2-furylboronic acid

The present invention refers to an improved method of producing 5-formyl-2-furylboronic acid. The method is carried out in a three-step process comprising the steps of:a) addition of a base to a composition comprising a boric acid ester and 2-furaldehyde whereby the formyl functionality of the 2-furaldehyde is protected with a protective group, andb) acidic work-up of the reaction mixture of step a), andc) isolation of 5-formyl-2-furylboronic acid.

5-formyl-2-furylboronic acid as a versatile bifunctional reagent for the synthesis of π-extended heteroarylfuran systems

5-Formyl-2-furylboronic acid reacts cleanly with a range of heteroaryl bromides under Suzuki-Miyaura cross-coupling conditions to produce 2-formyl-5-heteroarylfuran derivatives. Subsequent Wittig olefination reactions afford π-conjugated alkene-pyridyl-furan derivatives.