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Chemical Structure| 1312784-45-4 Chemical Structure| 1312784-45-4

Structure of 1312784-45-4

Chemical Structure| 1312784-45-4

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Product Details of [ 1312784-45-4 ]

CAS No. :1312784-45-4
Formula : C14H14ClFN2O2
M.W : 296.72
SMILES Code : FC1=CC=CC2=C1C(CC(OC(C)(C)C)=O)=NC(Cl)=N2
MDL No. :MFCD31558555

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Application In Synthesis of [ 1312784-45-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1312784-45-4 ]

[ 1312784-45-4 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 87611-00-5 ]
  • [ 321745-86-2 ]
  • [ 1312784-45-4 ]
YieldReaction ConditionsOperation in experiment
45% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane;palladium diacetate; In tetrahydrofuran; diethyl ether; at 45 - 48℃; for 40.0h;Inert atmosphere; Preparation of tert-butyl 2-(2-chloro-5-fluoroquinazolin-4-yl)acetate To a solution of <strong>[87611-00-5]2,4-dichloro-5-fluoroquinazoline</strong> (1.88 g, 8.64 mmol, Accela ChemBio) in THF (21.6 mL) under a nitrogen atmosphere was added (2-tert-butoxy-2-oxoethyl)zinc(II) chloride (0.5 M solution in Et2O, 51.8 mL, 25.9 mmol, Rieke Metals). Nitrogen was bubbled through the solution for about 20 min. Palladium(II) acetate (0.097 g, 0.432 mmol) and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.355 g, 0.864 mmol) were added to the reaction, each in one portion, and nitrogen was bubbled through the solution for about 5 min. The reaction solution was warmed to about 45 C. for about 24 h. After allowing to cool to ambient temperature, (2-tert-butoxy-2-oxoethyl)zinc(II) chloride (0.5 M solution in Et2O, 20.0 mL, 10.0 mmol, Rieke Metals), Pd(OAc)2 (0.097 g, 0.432 mmol), and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.355 g, 0.864 mmol) were added respectively. Nitrogen was bubbled through the solution for about 20 min and the reaction was warmed to about 48 C. for about 16 h. After cooling to ambient temperature, saturated aqueous NaHCO3 (90 mL) and EtOAc (100 mL) were added. The solid was removed by filtration. The layers were separated and the aqueous phase was extracted with EtOAc (100 mL). The combined organics were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with a gradient of 0-30% EtOAc in heptane. The product containing fractions were concentrated under reduced pressure and the residue was triturated with EtOAc. The solid was removed by filtration and the organics were concentrated under reduced pressure to afford tert-butyl 2-(2-chloro-5-fluoroquinazolin-4-yl)acetate (1.14 g, 45% yield): LC/MS (Table 1, method c) Rt=2.64 min; MS m/z: 297 (M+H)+.
 

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