2-(4-CHLORO-PHENYL)-OXAZOLE-4-CARBOXYLIC ACID ETHYL ESTER synthesis

8synthesis methods

Product Name:2-(4-CHLORO-PHENYL)-OXAZOLE-4-CARBOXYLIC ACID ETHYL ESTER
CAS Number:78979-62-1
Molecular formula:C12H10ClNO3
Molecular Weight:251.67

1679-18-1 Synthesis

1679-18-1
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460081-18-9 Synthesis

460081-18-9
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2-(4-CHLORO-PHENYL)-OXAZOLE-4-CARBOXYLIC ACID ETHYL ESTER

78979-62-1
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Yield:-

Reaction Conditions:

with 1,1'-bis-(diphenylphosphino)ferrocene;tetrakis(triphenylphosphine) palladium⁽⁰⁾;potassium carbonate in water;toluene at 90; for 12 h;Suzuki Coupling;

Steps:

General procedure for the synthesis of intermediate 55 by Suzuki coupling (step c)

General procedure: Toan oven-dried round bottom flask charged withethyl 2-chlorothiazole-4-carboxylate(500 mg, 2.60 mmol, 1.0 equiv.), toluene (10 mL),Pd(PPh₃)₄(150 mg, 0.13 mmol, 0.05 equiv.), DPPF (43 mg, 0.08 mmol, 0.03 equiv.), and saturated aqueous K₂CO₃solution (720 mg, 5.20 mmol, 2.0 equiv. in 1mL H₂O) was added 4-chlorophenylboronic acid(813 mg, 5.20 mmol, 2.0 equiv.).The reaction mixture was allowed to stir at 90^oC for 12 h. The reaction mixture wascooled to room temperature, 2N NaOH solution and the resulting mixture was extracted with EtOAc. The organic layer was dried over MgSO₄, filtered, and concentrated under reduced pressure. The residue was purified byMPLC (24g-silica-gel,n-hexanes/EtOAc)to affordethyl 2-(4-chlorophenyl)thiazole-4-carboxylate.

References:

Jung, Hui Jin;Nam, Eun Hye;Park, Jin Young;Ghosh, Prithwish;Kim, In Su [Bioorganic and Medicinal Chemistry Letters,2021,vol. 37,art. no. 127846] Location in patent:supporting information

23012-14-8 Synthesis