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ChemicalBook CAS DataBase List Methyl 2-bromo-5-isopropyl-1,3-thiazole-4-carboxylate
81569-28-0

Methyl 2-bromo-5-isopropyl-1,3-thiazole-4-carboxylate synthesis

1synthesis methods
-

Yield:81569-28-0 60%

Reaction Conditions:

with copper(I) bromide;isopentyl nitrite in acetonitrile at 80; for 3 h;

Steps:

42A Methyl 2-bromo-5-isopropylthiazole-4-carboxylate

To a solution of methyl 2-amino-5-isopropylthiazole-4-carboxylate (1.000 g, 4.99 mmol) in CH3CN (10 mL) was added isopentyl nitrite (1.073 mL, 7.99 mmol) followed by copper(I) bromide (1.433 g, 9.99 mmol) and the resulting mixture was heated at 80 °C for 3 h. The reaction mixture was then concentrated under reduced pressure and the residue was partitioned between EtOAc and water. The organic phase was separated, filtered through a CELITE pad and concentrated. The residue was purified on the ISCO using a REDISEP 24 g column (0 to 40% EtOAc-hexanes) to give the desired product as a light red oil (0.787 g, 60%). LCMS (APCI): calcd for C8H11BrNO2S [M+H]+ m/z 263.962, found 264.0. 1H NMR (CDCl3, 400 MHz) δ ppm: 4.17 (dt, J= 13.7, 6.8 Hz, 1H), 3.94 (s, 3H), 1.35 (s, 3H), 1.33 (s, 3H).

References:

WO2013/163279,2013,A1 Location in patent:Paragraph 00192