Diisopropylamine → HCID 178434440, compound

Temperature

0 °C

Normal-butyllithium (a 2.6 M solution in hexane, 87.0 mL) was dropwise added to a solution of N,N-diisopropylamine (11.2 mL) in THF (100 mL) at −78° C. under a nitrogen atmosphere, followed by increasing the temperature to 0° C. Then, the solution was cooled to −78° C., and a solution of 2-fluoropyridine (6.2 g) in THF (100 mL) was dropwise added thereto at −78° C., followed by stirring for 1 hr. Subsequently, a solution of N-methoxy-N-methylacetamide (8.46 mL) in THF (50 mL) was dropwise added to the reaction solution at −78° C., and then hydrazine monohydrate (31.9 mL) was added thereto, followed by stirring at 60° C. for 1 hr. After distillation of the solvent, water was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline. The organic layer after the washing was dried over anhydrous sodium sulfate, and then the solvent was distilled away to obtain compound (2a) (5.90 g, 69%) as a white solid.

1. temperatureThen, the solution was cooled to −78° C.
2. customat −78° C.
3. stirringby stirring at 60° C. for 1 hr
4. distillationAfter distillation of the solvent, water
5. additionwas added to the residue
6. extractionfollowed by extraction with ethyl acetate
7. washThe organic layer was washed with saturated saline
8. dry with materialThe organic layer after the washing was dried over anhydrous sodium sulfate
9. distillationthe solvent was distilled away

ORD record

ord-047fbe4925f54cae96792fa1e1394f97

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08779142B2