Bromine → HCID 71185714, compound

Temperature

25 °C

Liquid bromine (0.30 g, 0.097 ml, 1.89 mmol) was added drop wise to a stirred solution (5-(4-methoxyphenyl)-4-methylthiazol-2-yl)(piperidin-1-yl)methanone (5a, 0.5 g, 1.58 mmol) in acetic acid (6 ml) at 25° C. The resulting mixture was stirred at 25° C. for 3 hrs. 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 (50 ml). The mixture was then washed with saturated sodium bicarbonate solution (20 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 5b (0.54 g, 86.0%).

1. concentrationThe reaction mixture was then concentrated under reduced pressure
2. customThe residue obtained
3. concentrationafter concentration
4. dissolutionwas dissolved in ethyl acetate (50 ml)
5. washThe mixture was then washed with saturated sodium bicarbonate solution (20 ml)
6. concentrationThe separated organic layer was concentrated under reduced pressure
7. customto obtain a crude product, which
8. customwas then purified by flash column chromatography

ORD record

ord-93e3b2df1b3442c0bbca1a41b6090fbd

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946432B2