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5-[4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl]-2-furaldehyde
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Name

5-[4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl]-2-furaldehyde

 EINECS 1806241-263-5
CAS No. 231278-84-5 Density 1.407 g/cm3
PSA 77.25000 LogP 6.89040
Solubility N/A Melting Point 227.0 to 231.0 °C
Formula C26H17ClFN3O3 Boiling Point 650.3 °C at 760 mmHg
Molecular Weight 473.891 Flash Point 347.1 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 231278-84-5 (5-[4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl]-2-furaldehyde) Hazard Symbols N/A
Synonyms

[5-[4-[4-[(3-Fluorobenzyl)oxy]-3-chloroanilino]-6-quinazolinyl]-2-furancarboxaldehyde;

Article Data 39

5-[4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl]-2-furaldehyde Synthetic route

27329-70-0

5-formylfurane-2-boronic acid

N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-iodoquinazolin-4-amine

N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-iodoquinazolin-4-amine

231278-84-5

5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde

Conditions
ConditionsYield
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-formylfuran-2-boric acid

231278-20-9

N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-iodoquinazolin-4-amine

231278-84-5

5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde

Conditions
ConditionsYield
With palladium 10% on activated carbon; triethylamine In methanol; 1,2-dimethoxyethane; water at 50℃; for 24h;95.5%
With palladium 10% on activated carbon; triethylamine In methanol; 1,2-dimethoxyethane at 50℃; for 24h;95.5%
With triethylamine; bis-triphenylphosphine-palladium(II) chloride In methanol for 2h; Reflux;
98-01-1

furfural

231278-20-9

N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-iodoquinazolin-4-amine

231278-84-5

5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde

Conditions
ConditionsYield
Stage #1: furfural With n-butyllithium; N,O-dimethylhydroxylamine*hydrochloride In tetrahydrofuran; hexane at -20℃; for 1.25h;
Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at -15℃; for 0.25h;
Stage #3: N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-iodoquinazolin-4-amine With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine In tetrahydrofuran; ethanol; hexane at 60℃; Suzuki coupling;		95%
851684-46-3

N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-iodoquinazolin-4-amine hydrochloride

27329-70-0

5-formylfurane-2-boronic acid

231278-84-5

5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde

Conditions
ConditionsYield
With triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In ethanol for 2h; Heating / reflux;94%
1603976-11-9

5-(4,4,6-trimethyl-1,3,2-dioxaborinan-2-yl)furan-2-carbaldehyde

231278-20-9

N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-iodoquinazolin-4-amine

231278-84-5

5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde

Conditions
ConditionsYield
With palladium 10% on activated carbon; N-ethyl-N,N-diisopropylamine In methanol; ethanol at 90℃; for 2.5h;90%
1218791-07-1

5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)furan-2-carbaldehyde

231278-20-9

N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-iodoquinazolin-4-amine

231278-84-5

5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde

Conditions
ConditionsYield
With palladium 10% on activated carbon In methanol for 8h; Reflux;89%
273731-82-1

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde

231278-20-9

N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-iodoquinazolin-4-amine

231278-84-5

5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde

Conditions
ConditionsYield
With palladium 10% on activated carbon; N-ethyl-N,N-diisopropylamine In methanol for 8h; Reflux;87%
27329-70-0

5-formylfurane-2-boronic acid

N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-iodoquinazolin-4-amine hydrochloride

231278-84-5

5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde

Conditions
ConditionsYield
With 5%-palladium/activated carbon; triethylamine In methanol; 1,2-dichloro-ethane at 50℃; for 16h;86%
With 5%-palladium/activated carbon; triethylamine In methanol; dichloromethane at 50℃; for 16h;86%

C8H13BrO4

6-cyano-4-[3-chloro-4-(3-fluorobenzyloxy)phenyl]aminoquinazoline

231278-84-5

5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde

Conditions
ConditionsYield
Stage #1: C8H13BrO4 With iodine; magnesium In 2-methyltetrahydrofuran; ethylene dibromide at 30 - 45℃; for 5h;
Stage #2: 6-cyano-4-[3-chloro-4-(3-fluorobenzyloxy)phenyl]aminoquinazoline In 2-methyltetrahydrofuran; ethylene dibromide at 20 - 30℃; for 5h;
Stage #3: With hydrogenchloride In 2-methyltetrahydrofuran; water; ethylene dibromide at 50 - 55℃; for 4h;		84.1%

1,1,2,2-tetramethoxy-4-bromobutane

6-cyano-4-[3-chloro-4-(3-fluorobenzyloxy)phenyl]aminoquinazoline

231278-84-5

5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde

Conditions
ConditionsYield
Stage #1: 1,1,2,2-tetramethoxy-4-bromobutane With magnesium In tetrahydrofuran; ethylene dibromide at 30 - 45℃; for 4h;
Stage #2: 6-cyano-4-[3-chloro-4-(3-fluorobenzyloxy)phenyl]aminoquinazoline In tetrahydrofuran; ethylene dibromide at 15 - 30℃; for 2h;
Stage #3: With hydrogenchloride In tetrahydrofuran; water; ethylene dibromide at 50 - 55℃; for 4h;		82.8%

5-[4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl]-2-furaldehyde Chemical Properties

Molecular Structure of 5-[4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl]-2-furaldehyde (CAS NO.231278-84-5):

Empirical Formula: C26H17ClFN3O3
Molecular Weight: 473.8829
H bond acceptors: 6
H bond donors: 1
Freely Rotating Bonds: 6
Polar Surface Area: 68.46 Å2
Index of Refraction: 1.694
Molar Refractivity: 129.35 cm3
Molar Volume: 336.6 cm3
Surface Tension: 60 dyne/cm
Density: 1.407 g/cm3
Flash Point: 347.1 °C
Enthalpy of Vaporization: 95.85 kJ/mol
Boiling Point: 650.3 °C at 760 mmHg
Vapour Pressure: 8.52E-17 mmHg at 25°C
Product Categories: Various Intermediates; Intermediates; Intermediates & Fine Chemicals; Pharmaceuticals

5-[4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl]-2-furaldehyde Specification

  5-[4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl]-2-furaldehyde , with CAS number of 231278-84-5, can be called [5-[4-[4-[(3-Fluorobenzyl)oxy]-3-chloroanilino]-6-quinazolinyl]-2-furancarboxaldehyde ; 5-[4-[[3-Chloro-4-[(3-fluorophenyl)methoxy]phenyl]amino]-6-quinazolinyl]-2-furancarboxaldehyde ; 5-[4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl]-2-furaldehyde . 5-[4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl]-2-furaldehyde (CAS NO.231278-84-5) can be used as a lapatinib intermediate.

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