Tetrahydrofuran → HCID 90373278, compound

Temperature

30 °C

To a 1000 mL, 3-neck, round-bottomed flask equipped with an internal temperature probe was added 1-(6-bromo-3-fluoro-4-(triethylsilyl)pyridin-2-yl)-2-fluoroethanone (35 g, 100 mmol), THF (350 mL), (R)-2-methylpropane-2-sulfinamide (AK Scientific; 25.4 g, 210 mmol) and titanium (iv) ethoxide (Aldrich; 51.7 mL, 250 mmol). The solution was heated and stirred at 30° C. for 15 h and then at 40° C. for 2 h. The solution was allowed to cool to rt and then brine (200 mL) was added followed by EtOAc (200 mL). A white precipitate formed. The solution was filtered through Celite (600 mL medium fritted funnel) and the filtercake was washed with EtOAc. The filtrate was washed with brine, dried (Na2SO4) and concentrated to afford the crude product as a yellow semi-solid. The material was dissolved in 20% EtOAc/hexane (300 mL) and washed with water (2×100 mL) and brine (100 mL) and then dried and concentrated to afford (R,E)-N-(1-(6-bromo-3-fluoro-4-(triethylsilyl)pyridin-2-yl)-2-fluoroethylidene)-2-methylpropane-2-sulfinamide (37.8 g, 83 mmol, 84% yield) as a yellow oil which was carried on directly. MS m/z=453.0 [M+H]+. Calculated for C17H27BrF2N2OSSi: 452.1.

1. customTo a 1000 mL, 3-neck, round-bottomed flask equipped with an internal temperature probe
2. temperatureThe solution was heated
3. waitat 40° C. for 2 h
4. temperatureto cool to rt
5. customA white precipitate formed
6. filtrationThe solution was filtered through Celite (600 mL medium fritted funnel)
7. washthe filtercake was washed with EtOAc
8. washThe filtrate was washed with brine
9. dry with materialdried (Na2SO4)
10. concentrationconcentrated
11. customto afford the crude product as a yellow semi-solid
12. washwashed with water (2×100 mL) and brine (100 mL)
13. customdried
14. concentrationconcentrated

ORD record

ord-4b9ddcabea424f50992b7967a1b428ac

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296734B2