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8-Chloro-4-(6-chloro-2,3-dihydro-indol-1-yl)-quinazoline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
47%
Example 98 8-Chloro-4-(6-chloro-2,3-dihydro-indol-1-yl)-quinazoline Utilizing a procedure analogous to that described in Example 24, this product was prepared in 47% yield from <strong>[52537-00-5]6-chloro-indoline</strong> and 4,8-dichloro-quinazoline. (M.P. 190 C.; LC-MS: 316 (MH+)).
A stream of nitrogen gas was bubbled through a mixture of 4,8- dichloroquinazoline (1.75 g, 8.8 mmol), <strong>[89694-46-2]2-chloro-5-methoxyphenylboronic acid</strong> (1.97 g, 10.6 mmol), 2M aqueous Na2CO3 (11 mL, 22 mmol) in dimethoxyethane (15 mL) and water (4 mL) for 10 min. Tetrakis-triphenylphosphine palladium (521 mg, 0.44 mmol) was added and the mixture was stirred at 75 0C for 6 h. The suspension was cooled and partitioned between EtOAc (60 mL) and water (30 mL). The layers were separated and the organic layer was further washed with aqueous NaHCO3 (10 mL), water (10 mL), and brine (20 mL). The organic layer was dried with Na2SO4 and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with a gradient of 0:100 to 20:80 E:H to afford white foamy solid. MS (ESI) m/z 305.0; HRMS: calcd for CI5HI0CI2N2O + H+, 305.02429; found (ESI, [M+H]+ Obs'd), 305.0247.
Chemistry
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Material Science
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120K+ Compounds
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