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433283-22-8

RAC-5-(4-FLUOROPHENYL)-2-METHYL-1,3-THIAZOLE-4-CARBOXYLIC ACID synthesis

3synthesis methods
1007873-79-1 Synthesis
METHYL 5-(4-FLUOROPHENYL)-2-METHYLTHIAZOLE-4-CARBOXYLATE

1007873-79-1
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Yield:433283-22-8 93%

Reaction Conditions:

Stage #1: methyl 5-(4-fluorophenyl)-2-methyl-1,3-thiazole-4-carboxylatewith water;sodium hydroxide in tetrahydrofuran;methanol at 20; for 0.5 h;
Stage #2: with hydrogenchloride in water at 0; for 0.25 h;

Steps:

3.c

To a solution of 5-(4-fluoro-phenyl)-2-methyl-thiazole-4-carboxylic acid methyl ester (15 g) in a mixture of THF (60 mL) and MeOH (20 mL) was added a solution of sodium hydroxide (2.63 g) in water (60 mL). The reaction mixture was stirred at RT for 30 min. The reaction mixture was then concentrated in vacuo, and the residue was dissolved with water (100 mL) and concentrated again in vacuo. The residue was dissolved in water (250 mL), cooled to 0° C. with a ice-bath. Then was added a solution of conc.HCl (37%)(7.72 g) in water (7.72 g) and stirred at 0° C. for 15 min. The resulting precipitate was filtered off, washed with water and dried in high vacuum pump. to give the title compound as a white solid (13.16 g, 93%).1H-NMR (DMSO-d6): δ=2.67 (s, 3H); 7.27 (m, 2H); 7.53 (m, 2H); 12.89 (br.s, 1H).

References:

US2010/222600,2010,A1 Location in patent:Page/Page column 23

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