Cesium carbonate → (R)-N-((S)-1-(4-cyclopropyl-2-fluorophenyl)ethyl)-2-methylpropane-2-sulfinamide

Temperatur

100 °C

To a microwave vial containing a stir bar was added (R)—N—((S)-1-(4-bromo-2-fluorophenyl)ethyl)-2-methylpropane-2-sulfinamide (100 mg, 0.31 mmol) followed by the addition of potassium cyclopropyltrifluoroborate (459 mg, 3.10 mmol), cesium carbonate (506 mg, 1.55 mmol) and Pd(OAc)2 (7 mg, 0.03 mmol) and di(1-adamantyl)-n-butylphosphine (22 mg, 0.06 mmol), toluene (2.6 mL) and finally water (0.5 mL). The vial capped and heated by microwave irradiation for 20 min at 100° C., followed by thermal heating at 100° C. in a preheated aluminum tray for 18 hours. The reaction mixture was diluted with a saturated solution of NH4Cl. The aqueous mixture extracted with EtOAc. Organic phases combined, washed with water, brine, dried (Na2SO4), filtered and concentrated to afford a yellow crystalline of (R)—N—((S)-1-(4-cyclopropyl-2-fluorophenyl)ethyl)-2-methylpropane-2-sulfinamide (116 mg, 0.33 mmol, 106% yield). LCMS m/z 284.0 (M+H)+, Rt 0.90 min.

1. additionTo a microwave vial containing a stir bar
2. customThe vial capped
3. extractionThe aqueous mixture extracted with EtOAc
4. washwashed with water, brine
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated

ORD-Eintrag

ord-867506725c25429da721aca0984f0209

Quelldatensatz

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08957068B2