Ethyl bromoacetate → Pyridazineacetic acid, 1-, (6H), 3-chloro-6-oxo-, ethyl ester

To a solution of 6-chloropyridazin-3-ol (0.5 g, 3.83 mmol, WO2011015629) in DMF (5 mL) was added potassium carbonate (1.059 g, 7.66 mmol, Rankem) followed by ethyl 2-bromoacetate (0.960 g, 5.75 mmol, Spectrochem). The reaction mixture was stirred at RT for 5 h. The reaction mixture was quenched with water (2 mL) and the product was extracted with EtOAc (3×20 mL). Combined organic layers were washed successively with water (20 mL) and brine (20 mL). The organic layer was dried over sodium sulphate and evaporated under vacuum to afford ethyl 2-(3-chloro-6-oxopyridazin-1(6H)-yl)acetate 0.5 g (60.3%) as pale yellow solids. 1H NMR (400 MHz, CDCl3): δ 7.266-7.236 (d, J=12 Hz, 1H), 6.965-6.945 (d, J=7.6 Hz, 1H) 4.819 (s, 2H) 4.273-4.230 (m, 2H) 1.309-1.279 (m, 3H); MS m/z=217.2 (M+H)+.

1. customThe reaction mixture was quenched with water (2 mL)
2. extractionthe product was extracted with EtOAc (3×20 mL)
3. washCombined organic layers were washed successively with water (20 mL) and brine (20 mL)
4. dry with materialThe organic layer was dried over sodium sulphate
5. customevaporated under vacuum

ORD record

ord-331b298b90dc406bac6f9ebccff84bbc

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09029409B2