Sodium hydride → HCID 86588636, compound

A solution of (3-fluoro-benzyl)-carbamic acid tert-butyl ester I-4a (1.21 g, 5.37 mmol) in DMF (50 mL) was treated with 60% NaH in mineral oil (430 mg, 10.7 mmol). The resulting mixture was stirred at ambient temperature until the gas evolution ceased. The solution was treated with 2,6-dichloro-pyrazine (800 mg, 5.37 mmol) and the reaction mixture was heated to 80° C. under N2 and stirred for 5 h. The reaction was cooled and concentrated in vacuo to approximately ⅓ volume. The reaction mixture was poured into H2O (50 mL) and extracted with Ethyl Acetate (1×200 mL). The organic layer was washed with H2O (4×50 mL), brine, dried (Na2SO4), and concentrated to dryness. The crude product was purified by chromatography (EtOAc/Hex 5:95) to afford the title compound I-4b (1.14 g) as a colorless oil.

1. temperaturethe reaction mixture was heated to 80° C. under N2
2. stirringstirred for 5 h
3. temperatureThe reaction was cooled
4. concentrationconcentrated in vacuo to approximately ⅓ volume
5. additionThe reaction mixture was poured into H2O (50 mL)
6. extractionextracted with Ethyl Acetate (1×200 mL)
7. washThe organic layer was washed with H2O (4×50 mL), brine
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated to dryness
10. customThe crude product was purified by chromatography (EtOAc/Hex 5:95)

ORD record

ord-03d55f2743534f9b9189c9a7fb6f169a

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06894050B2