Bromine → HCID 71185511, compound

Temperature

25 °C

Liquid bromine (1.04 g, 0.36 ml, 6.49 mmol) was added to a stirred solution of ethyl 5-(4-methoxyphenyl)-4-methylthiazole-2-carboxylate (prepared according to the procedure reported in WO 2006/089076, 1.5 g, 5.41 mmol) in acetic acid (15 ml) at 25° C. The resulting reaction mixture was then stirred at 25° C. for 3 hours. The progress of the reaction was monitored by TLC. The reaction mixture was then concentrated under reduced pressure. The residue obtained after concentration was dissolved in ethyl acetate (100 ml). The mixture obtained was washed with saturated sodium bicarbonate solution (30 ml). The separated organic layer was concentrated under reduced pressure to obtain a crude product, which was then purified by flash column chromatography using 30% ethyl acetate in hexanes as an eluent to obtain the title compound 8a (1.70 g, 88.5%).

1. customprepared
2. customat 25° C
3. customThe resulting reaction mixture
4. concentrationThe reaction mixture was then concentrated under reduced pressure
5. customThe residue obtained
6. concentrationafter concentration
7. dissolutionwas dissolved in ethyl acetate (100 ml)
8. customThe mixture obtained
9. washwas washed with saturated sodium bicarbonate solution (30 ml)
10. concentrationThe separated organic layer was concentrated under reduced pressure
11. customto obtain a crude product, which
12. customwas then purified by flash column chromatography

ORD record

ord-e444751e48b2441788481cca427b76ee

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946432B2