27329-70-0

Basic information

• Product Name: 2-Formylfuran-5-boronic acid
• Synonyms: FFBA;CHEMBRDG-BB 3200975;5-FORMYL-2-FURANBORONIC ACID;5-FORMYL-2-FURYLBORONIC ACID;(5-FORMYL-2-FURANYL)BORONIC ACID;5-FORMYLFURAN-2-BORONIC ACID;AKOS BRN-0038;2-FORMYLFURAN-5-BORONIC ACID
• CAS NO: 27329-70-0
• Molecular Formula: C₅H₅BO₄
• Molecular Weight: 139.9
• EINECS: 1312995-182-4
• Product Categories: OLED materials,pharm chemical,electronic;Boronate Ester;Potassium Trifluoroborate;Lapatinib;Pyrans;Aldehydes;blocks;BoronicAcids;Heterocycles;Boronic acids;Boronic Acid;Aldehyde;Furan;Organoborons;B (Classes of Boron Compounds);Boronic Acids;Boronic Acids and Derivatives;Heteroaryl
• Mol File: 27329-70-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 136 °C (dec.)(lit.)
• Boiling Point: 379.3 °C at 760 mmHg
• Flash Point: 183.2 °C
• Appearance: beige to brown powder
• Density: 1.36 g/cm³
• Vapor Pressure: 1.98E-06mmHg at 25°C
• Refractive Index: 1.51
• Storage Temp.: 0-6°C
• Solubility: 1.38g/l
• PKA: 7.11±0.53(Predicted)
• Water Solubility: Insoluble in water.
• Sensitive: Air Sensitive
• BRN: 1637050
• CAS DataBase Reference: 2-Formylfuran-5-boronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Formylfuran-5-boronic acid(27329-70-0)
• EPA Substance Registry System: 2-Formylfuran-5-boronic acid(27329-70-0)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-36/37/38
• Safety Statements: 26-36/37/39-45-37/39-27
• RIDADR: UN 3261 8/PG 3
• WGK Germany: 3
• TSCA: No
• HazardClass: IRRITANT, KEEP COLD
• PackingGroup: Ⅲ
• Hazardous Substances Data: 27329-70-0(Hazardous Substances Data)

Usage

Chemical Properties

beige to brown powder

Uses

Different sources of media describe the Uses of 27329-70-0 differently. You can refer to the following data:
1. suzuki reaction
2. As a bifunctional reagent used in the synthesis of π -extended heteroarylfuran systems. Reactant involved in Suzuki coupling for synthesis of stable dye-sensitized solar cells. Reactant involved in synthesis of biologically active molecules including, heteroarylation for the synthesis of HIF-1 inhibitors, disalicylic acid-furanyl derivatives to inhibit ephrin binding, HIV-1 integrase inhibitors, epidermal growth factor receptor inhibitors.

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

Downstream Products

• 13803-39-9 5-phenylfuran-2-carbaldehyde 
• 52130-30-0 5-[3-(trifluoromethyl)phenyl]furan-2-carbaldehyde 
• 32364-30-0 5-(thiophen-2-yl)furan-2-carboxaldehyde 
• 13148-43-1 5-(3-nitrophenyl)furfural 
• 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 
• 38588-49-7 5-(pyridin-3-yl)-furan-2-carbaldehyde 
• 88460-72-4 2-(5-formylfuran-2-yl)benzoic acid 
• 627906-59-6 5-(4-hydroxy-3-methylphenyl)-2-furanecarboxaldehyde 
• 388082-75-5 5-(4-[3-chloro-4-(3-fluorobenzyloxy)-anilino]-6-quinazolinyl)-furan-2-carbaldehyde 4-methylbenzenesulfonate 
• 909393-03-9 2-[6-(5-formylfuran-2-yl)-2-(3-methoxyphenyl)-4-oxo-4H-quinazolin-3-yl]-isopropylacetamide 

Relevant articles and documents

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.

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 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.