Sodium hydride → HCID 118093886, Verbindung

A solution of cyclopropyl carbinol (0.269 mL, 3.40 mmol) in tetrahydrofuran (6.9 mL) at 0° C. was treated with sodium hydride (0.0860 g, 3.40 mmol) and stirred at RT for 30 min. The reaction mixture was cooled to 0° C., treated with 4-bromo-3-fluoro-2-nitroaniline (0.400 g, 1.70 mmol) [Combi-Blocks, AN-2785] and stirred at RT for 15 h. The reaction mixture was cooled to 0° C. and quenched with saturated ammonium chloride solution. The reaction mixture was diluted with ethyl acetate (50 mL) and water (40 mL). The organic layer was washed with brine, dried with sodium sulfate, filtered, and concentrated to give crude oil. Purification by flash column chromatography (100% hexanes to 40% EtOAc/hexanes) gave the desired product (0.365 g, 75%). LCMS calculated for C10H12BrN2O3 (M+H)+: m/z=287.1. found: 286.8.

1. temperatureThe reaction mixture was cooled to 0° C.
2. stirringAN-2785] and stirred at RT for 15 h
3. temperatureThe reaction mixture was cooled to 0° C.
4. customquenched with saturated ammonium chloride solution
5. additionThe reaction mixture was diluted with ethyl acetate (50 mL) and water (40 mL)
6. washThe organic layer was washed with brine
7. dry with materialdried with sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customto give crude oil
11. customPurification by flash column chromatography (100% hexanes to 40% EtOAc/hexanes)

ORD-Eintrag

ord-40b72ab176634df0be5e3b662e1a16f4

Quelldatensatz

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09399640B2