Hydrochloric Acid → HCID 58645619, compound

Temperature

0 °C

Dissolve 2,2,6,6-tetramethylpiperidine (19.3 g, 136 mmol) in dry THF (300 mL). Cool the solution to 0° C., and slowly add n-BuLi (2.5M Hexanes; 50 mL, 125 mmol). Stir the mixture at 0° C. for ten minutes, and then cool to −78° C. Add this solution via canula to a mixture of ethyl 6-ethoxy-4-(trifluoromethyl)pyridazine-3-carboxylate (15.0 g, 56.8 mmol; prepared essentially as described by Guillaume et al. (1995) Synthesis 8:920-922) and dibromomethane (23.6 g, 136 mmol) in dry THF (300 mL) at −78° C. Stir the mixture at −78° C. for 30 minutes. Quench the reaction with water (200 mL) and allow it to warm to room temperature. Add brine (100 mL) and 3N HCl (100 mL). Extract with EtOAc (3×300 mL). Dry the combined organic extracts over sodium sulfate and evaporate. Chromatograph on silica eluting first with hexane followed by hexane/EtOAc (95/5) to yield the title compound. LC/MS (MH+) 392.87.

1. temperaturecool to −78° C
2. additionAdd this solution via canula
3. customprepared essentially
4. stirringStir the mixture at −78° C. for 30 minutes
5. customQuench
6. customthe reaction with water (200 mL)
7. temperatureto warm to room temperature
8. extractionExtract with EtOAc (3×300 mL)
9. dry with materialDry the combined organic extracts over sodium sulfate
10. customevaporate

ORD record

ord-ddd8d0237d3d4c73b47a85a06686f9d1

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07935702B2