Category: 1194374-25-8

1194374-25-8, 2-Bromo-5-methylthiazole-4-carboxylic acid is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 2-(2-Methoxy-3-nitro-phenyl)-5-methyl-thiazole-4-carboxylic acid; 2-(2-Methoxy-3-nitro-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 6a (1.7 g, 6.08 mmol), 2-bromo-5-methyl-thiazole-4-carboxylic acid (900 mg, 4.05 mmol), tetrakis (triphenylphosphine)palladium (233 mg, 0.2 mmol) and sodium carbonate (1.29 g, 12.16 mmol) were dissolved in 30 mL of 1,4-dioxane. The reaction mixture was heated to reflux for 4 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was diluted with 20 mL of hydrochloric acid (1 N) and 30 mL of ethyl acetate. The separated organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The residue was recrystallized from a solvent mixture of ethyl acetate and hexane to obtain the title compound 2-(2-methoxy-3-nitro-phenyl)-5-methyl-thiazole-4-carboxylic acid 47a (310 mg, yield 26%) as a yellow solid. MS m/z (ESI): 292.6 [M-1] 1H NMR (400 MHz, DMSO-d6): delta 13.45 (br, 1H), 8.58 (dd, J = 8.0, 1H), 8.14 (dd, J = 8.0,1H), 7.52 (t, J = 8.0, 1H), 3.93 (s, 3H), 2.71 (s, 3H), 1194374-25-8

Big data shows that 1194374-25-8 is playing an increasingly important role.

Reference：
Patent; Jiangsu Hengrui Medicine Co., Ltd.; Shanghai Hengrui Pharmaceutical Co. Ltd.; EP2236500; (2010); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1194374-25-8,2-Bromo-5-methylthiazole-4-carboxylic acid,as a common compound, the synthetic route is as follows.

2-Bromo-5-methylthiazole-4-carboxylic acid (118 mg, 0.5 32 mmol) was suspended in anhydrous DCM (5 mL), and a drop a DMF was added. Then, oxalyl chloride (2 M in DCM) (0.725 mL, 1.45 mmol) was added dropwise, and the reactionmixture was stirred for 1 h at rt (bubbling observed; the mixture became homogeneous). Then, DCM was removed under reduced pressure, and the obtained acid chloride (brown syrup) was used in the subsequent step. In a separate flask, to a suspension of Intermediate 2, HC1 (141 mg, 0.483 mmol) in THF (5 mL), was added DIEA (0.084 mL, 0.483 mmol) and trimethylsilyl cyanide (0.644 mL, 4.83 mmol). The resultant solutionwas stirred at rt for 10 mm, and then was treated with a solution of acid chloride obtained as described above in THF (5 mL). The mixture was stirred at 50 C for 1.5 h. The reaction mixture was concentrated, then trifluoroethanol (10 mL) was added. The residue was purified by flash chromatography (solid loading on CELITE, 0-100% EtOAc/Hex) affording Intermediate 24 (86 mg, 39% yield) as a off-white solid. MS(ESI) m/z: 459.0(M+H) ?H NMR: (400 MHz, CDC13) oe ppm 9.91 (s, 1H), 8.46 (dd, J7.8, 1.0 Hz, 1H),7.86 – 7.80 (m, 1H), 7.80 – 7.74 (m, 1H), 7.70 (d, J8.1 Hz, 1H), 7.37 (br d, J=7.9 Hz,1H), 4.47 (sxt, J=8.2 Hz, 1H), 3.83 (quin, J8.5 Hz, 1H), 2.77 – 2.69 (m, 1H), 2.63 – 2.34(m, 5H), 2.17 (dd,J=10.8, 8.8 Hz, 1H), 2.04- 1.97 (m, 1H), 1.60 (s, 3H)., 1194374-25-8

As the paragraph descriping shows that 1194374-25-8 is playing an increasingly important role.

Reference：
Patent; BRISTOL-MYERS SQUIBB COMPANY; LADZIATA, Vladimir; GLUNZ, Peter W.; HU, Zilun; WANG, Yufeng; (0 pag.)WO2016/10950; (2016); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica