6-BROMO-4-PHENYLQUINAZOLIN-2(1H)-ONE synthesis

4synthesis methods

Product Name:6-BROMO-4-PHENYLQUINAZOLIN-2(1H)-ONE
CAS Number:33443-53-7
Molecular formula:C14H9BrN2O
Molecular Weight:301.14

39263-32-6
243 suppliers
$15.00/1g

79-22-1
2 suppliers
$38.00/1000g

100-58-3
192 suppliers
$18.00/10ml

33443-53-7
15 suppliers
$416.00/1g

Yield:33443-53-7 82%

Reaction Conditions:

Stage #1: 2-amino-5-bromobenzonitrile;phenylmagnesium bromide in tetrahydrofuran;diethyl ether at 20 - 70; for 2 h;Inert atmosphere;
Stage #2: methyl chloroformate in tetrahydrofuran;diethyl ether at 70; for 15 h;Inert atmosphere;

Steps:

Typical procedure for Grignard/cyclization reaction

General procedure: All glassware was oven dried overnight and anhydrous solvent was obtained from an Innovative Technology Pure Solvent system. A solution of phenyl magnesium bromide in diethyl ether (13.3 mL of a 3.0 M solution, 40 mmol, 2 eq.) was added via syringe to a stirred, room temperature solution of 2-amino-5-bromobenzonitrile (3.94 g, 20 mmol, 1 eq.) in anhydrous THF (30 mL) under a nitrogen atmosphere. The reaction mixture was heated at 70 °C with stirring for 2 h, then cooled to room temperature and placed on an ice water bath. Methyl chloroformate (3.87 mL, 50 mmol, 2.5 eq.) was then added slowly dropwise via syringe. The reactions mixture was then heated to 70 °C with stirring for 3 h, and then maintained at room temperature for an additional 12 h. A solution of aqueous HCl (2 M, 40 mL) was added and the mixture was allowed to stir for 5 min. Saturated aqueous sodium bicarbonate was then added to neutralize the reaction mixture, which was then placed on ice water bath for 20 min. The resulting precipitate was then filtered through a fritted funnel and washed with H₂O (10 mL) followed by diethyl ether (5 mL) to give 4a (4.92 g, 82% yield), which was used without further purification unless otherwise noted.

References:

Pham, ThanhTruc;Walden, Madeline;Butler, Christopher;Diaz-Gonzalez, Rosario;Pérez-Moreno, Guiomar;Ceballos-Pérez, Gloria;Gomez-Pérez, Veronica;García-Hernández, Raquel;Zecca, Henry;Krakoff, Emma;Kopec, Brian;Ichire, Ogar;Mackenzie, Caden;Pitot, Marika;Ruiz, Luis Miguel;Gamarro, Francisco;González-Pacanowska, Dolores;Navarro, Miguel;Dounay, Amy B. [Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,# 16,p. 3629 - 3635] Location in patent:supporting information

39859-36-4 Synthesis