ChemicalBook CAS DataBase List 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 synthesis

7synthesis methods

Product Name:5-[4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl]-2-furaldehyde
CAS Number:231278-84-5
Molecular formula:C26H17ClFN3O3
Molecular Weight:473.88

27329-70-0 Synthesis

27329-70-0
466 suppliers
$6.00/1g

231278-20-9 Synthesis

N-[3-Chloro-4-(3-fluorobenzyloxy)phenyl]-6-iodoquinazolin-4-amine

231278-20-9
299 suppliers
$10.00/250mg

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

231278-84-5
286 suppliers
$8.00/250mg

Yield:231278-84-5 98.7%

Reaction Conditions:

with potassium carbonate;palladium diacetate in tetrahydrofuran;ethanol for 0.666667 h;Product distribution / selectivity;Reflux;

Steps:

13
Example 13: preparation of crystalline lapatinib aldehyde base[00098] To a 3L reactor lOOg of compound of formula C, 37.35g of 5-fo?nyl-2- furanboronic acid, 1.33g of palladium acetate, 54.66g of potassium carbonate, 750 ml of absolute ethanol and 750ml of THF were added. The suspension was stirred and heated to reflux (T(jacket) = 75°C) for 40 minutes. The reaction mixture was cooled to room temperature (T(jacket) = 20⁰C) and diluted with 750 ml of THF and 750 ml of absolute ethanol. The resulting mixture was stirred at 25⁰C for an hour. Inorganic salts were filtered off in vacuum, washed with 100 ml of absolute ethanol, 100 ml of THF and discarded. The filtrate combined with washings was transferred into a 1OL reactor equipped with a mechanical stirrer and a dropping funnel. 3L of water was added dropwise into the solution of lapatinib-aldehyde base in EtOH/THF (1 :1) for an hour (T(jacket) = 20⁰C). The resulting yellow suspension was stirred at RT (T(jacket) = 20⁰C) for 1.5 hour. The yellow solid was filtered in vacuum and washed over the filter with 100 ml of cold absolute ethanol. It was allowed to dry in a vacuum oven at 40⁰C for 16 hours, and additional 24 hours in vacuum oven at 60⁰C to give 92.56g of final product (Yield - 98.7%; Purity - 99.12%)

References:

TEVA PHARMACEUTICAL INDUSTRIES LTD.;TEVA PHARMACEUTICALS USA, INC.;METSGER, Leonid;YURKOVSKI, Slavik;GOROHOVSKY-ROSENBERG, Sofia;KIPNIS, Noa;LAVY, Dikla WO2010/17387, 2010, A2 Location in patent:Page/Page column 24

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