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ChemicalBook CAS DataBase List 4-Thiazolecarboxylic acid, 2-bromo-5-cyclopropyl-, methyl ester
1408235-82-4

4-Thiazolecarboxylic acid, 2-bromo-5-cyclopropyl-, methyl ester synthesis

5synthesis methods
4-Thiazolecarboxylic acid, 2-bromo-5-cyclopropyl-, methyl ester

1408235-82-4
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[2,2'-Bithiazole]-4-carboxylic acid, 5-cyclopropyl-, methyl ester

1408235-75-5
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Yield:1408235-75-5 750 mg

Reaction Conditions:

with palladium diacetate;triphenylphosphine in toluene at 80 - 90;Inert atmosphere;

Steps:

1

Compound 15 (1g, 3.82mmol) was dissolved in anhydrous toluene (20mL). The inner air was replaced by N2. The above-described Zinc reagent 14 is introduced into the reaction mixture, then the catalyst palladium acetate (43 mg, 0.19mmol) and triphenylphosphine (100 mg, 0.38mmol) were added. The reaction mixture was heated to 80-90□ for a while until the crude material compound 15 was all consumed. After removal of insoluble substance by filtration, the organic phase was concentrated and then diluted with CH2Cl2(50mL). After adding 1N HCl (30mL) with stirring for 10 min, the organic phase was separated. The aqueous phase was extracted by CH2Cl2 (30mL) twice. The combination of all extracted organic phases was concentrated and then subjected to silica gel column flash chromotography (PE/EtOAc = 4: 1) to obtain compound 16 (750 g, 73.5%, yellow grease), 1H NMR (300 MHz, CDCl3) δ 7.85 (d, J=3.0 Hz, 1H), 7.45 (d, J=3.0 Hz, 1H), 3.96 (s, 3H), 3.10-3.14 (m, 1H), 1.31-1.38 (m, 2H), 0.84-0.89 (m, 2H).

References:

EP2708534,2014,A1 Location in patent:Paragraph 0036