With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.167366-05-4,4-Bromo-2-formylthiazole,as a common compound, the synthetic route is as follows.
A toluene (120 mL) solution of 4-bromothiazole-2-carbaldehyde (7 g, 36.50 mmol) and ethyleneglycol (2.72 g, 43.7 mmol) in a RB flask was added catalytic amount of pTsOH (0.347 g, 1.823mmol). The RB flask was attached with Dean-Stark apparatus and reaction mixture was heated to reflux for 12h. The mixture was cooled to RT, and was partitioned with saturated aqueous NaHCO3 solution. The organic layer was separated, washed with saturated aqueous NaHCO3 (2 X 120 mL) solution and then once with brine (100 mL). The organic layer was dried over anhydroussodium sulphate, filtered and the filtrate concentrated under reduced pressure. The residue was purified by combiflash chromatography (40 g Redisep 5i02 column, eluting with 20% EtOAc in pet ether) to afford the title compound 137A (8 g, 97%) as a colourless liquid. LC-MS retention time = 1.557 mm; m/z = 236.0 [M+2Hj + K1NETIX XB-C18, (3 X 75) mm, 2.6 micron column; Flow rate: 1 mL/min; Mobile Phase A: 10mM HCO2NH4in 98% Water/ 2% ACN; Mobile PhaseB: 10 mM HCO2NH4 in 2% Water/ 98% ACN; 20% B to 100% B over 4.6 mm, then hold 0.5 mm. at 20% B with flow rate 1-1.5 mL/min; Detection: UV at 254 nm. ?H NMR (400 MHz, DMSO-d6) oe 7.94 (s, 1H), 6.08 (s, 1H), 3.99 -4.08 (m, 4H)., 167366-05-4
167366-05-4 4-Bromo-2-formylthiazole 2763187, athiazole compound, is more and more widely used in various fields.
Reference：
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHAO, Guohua; DEVASTHALE, Pratik; YE, Xiang-Yang; SELVAKUMAR, Kumaravel; DHANUSU, Suresh; BALASUBRAMANIAN, Palanikumar; GUERNON, Leatte R.; CIVIELLO, Rita; HAN, Xiaojun; PARKER, Michael F.; JACUTIN-PORTE, Swanee E.; (290 pag.)WO2018/89353; (2018); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica