2-(3-BROMO-PHENYL)-THIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER synthesis
- Product Name:2-(3-BROMO-PHENYL)-THIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER
- CAS Number:786654-97-5
- Molecular formula:C12H10BrNO2S
- Molecular Weight:312.18
Yield:786654-97-5 79%
Reaction Conditions:
in ethanol; for 16 h;Heating / reflux;
Steps:
1.a
Example 1; 2-tert-butoxycarbonylamino-3- [2- (3-dibenzofuran-4-yl-phenyl) - thiazol-4-ylmethylsulfanyl] -propionic acid; Preparation of 2- (3-bromo-phenyl) -thiazole-4-carboxylic acid ethyl ester; A solution of 3-bromo-thiobenzamide (6.4 g, 29.6 mmol) and 3-bromo-2-oxo-propionic acid ethyl ester (6.4 g, 33.1 mmol) in ethanol (50 mL, 0.6 M) is refluxed for 16 hours. After evaporation of the solvent, the residue is purified by flash chromatography (15% ethyl acetate in heptane) to give 2-(3-bromo-phenyl) -thiazole-4-carboxylic acid ethyl ester (7.3 g, 79%) as a white solid. 1H NMR (CDCl3, 300 MHz) δ 8.18-8.16(m, 2 H), 7.89 (dd, J1 = 1.8 Hz, J2 = 1.0 Hz, 1 H) , 7.56 (dd, J1 = 1.8 Hz, J2 = 1.0 Hz, 1 H), 7.31 (t, J = 7.9 Hz, 1 H), 4.44(q, J = 7.2 Hz, 2 H), 1.43 (t, J = 7.2 Hz, 3 H).
References:
WO2008/33934,2008,A1 Location in patent:Page/Page column 85
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