Ethyl bromopyruvate → Ethyl 6-chloroimidazo[1,2-a]pyridine-2-carboxylate

Temperature

60 °C

A solution of 2-amino-5-chloropyridine (2.0 g, 16 mmol) [Matrix Scientific, 021118] in acetone (39 mL) was treated with ethyl bromopyruvate (2.2 mL, 16 mmol) and heated at 60° C. for 45 min. The reaction mixture was cooled to 20° C. and the suspension was filtered. The solid that was collected was washed with a small amount of cold acetone and dried in vacuo. The solid was diluted with ethanol (12 mL) and water (19 mL), heated at 65° C., and treated with sodium bicarbonate (1.6 g, 19 mmol) portionwise. The reaction mixture was cooled to 20° C. and the suspension was filtered. The solid that was collected was washed with water (4×80 mL) and dried in vacuo to give the desired product (2.6 g, 74%). LCMS for C10H10ClN2O2 (M+H)+: m/z=225.1.

1. temperatureThe reaction mixture was cooled to 20° C.
2. filtrationthe suspension was filtered
3. customThe solid that was collected
4. washwas washed with a small amount of cold acetone
5. customdried in vacuo
6. additionThe solid was diluted with ethanol (12 mL) and water (19 mL)
7. temperatureheated at 65° C.
8. temperatureThe reaction mixture was cooled to 20° C.
9. filtrationthe suspension was filtered
10. customThe solid that was collected
11. washwas washed with water (4×80 mL)
12. customdried in vacuo

ORD record

ord-cac500a4670141ae9e11343abe1b26ed

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403847B2