Reaktion #1784890

Reaktionsgleichung

dichloromethane

potassium acetate

(2S,4R)-4-(4-bromo-2-(trifluoromethyl)phenylsulfonyl)-N-(1-cyanocyclopropyl)-1-(1-cyclobutyl-3-methyl-1H-pyrazol-5-yl)pyrrolidine-2-carboxamide

4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane)

→

crude title compound

4-((3R,5S)-5-(1-Cyanocyclopropylcarbamoyl)-1-(1-cyclobutyl-3-methyl-1H-pyrazol-5-yl)pyrrolidin-3-ylsulfonyl)-3-(trifluoromethyl)phenylboronic Acid

Lösungsmittel

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with iPrOAc (2×25 ml)
2. 2
   WaschenThe combined organic layers were washed with 0.1 N HCl/ice/brine (3×)
3. 3
   Trocknenicewater/brine (3×), dried over sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   SonstigeThe solvent was evaporated under reduced pressure

Vorschrift

A solution of (2S,4R)-4-(4-bromo-2-(trifluoromethyl)phenylsulfonyl)-N-(1-cyanocyclopropyl)-1-(1-cyclobutyl-3-methyl-1H-pyrazol-5-yl)pyrrolidine-2-carboxamide (40 mg, 66.6 umol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (33.8 mg, 133 umol; CAS Reg. No. 73183-34-3), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride 1:1 complex with dichloromethane (10.9 mg, 13.3 umol) and potassium acetate (32.7 mg, 333 umol) in DMSO (0.8 ml) was heated to 80° C. for 20 h. The reaction mixture was cooled to ambient temperature and poured onto 20 ml 0.1 N HCl/ice/brine and extracted with iPrOAc (2×25 ml). The combined organic layers were washed with 0.1 N HCl/ice/brine (3×), icewater/brine (3×), dried over sodium sulfate and filtered. The solvent was evaporated under reduced pressure to give the crude title compound (66 mg; quant.) which was used in the next reaction step without further purification. MS (ESI): m/z=566.2 [M+H]+.

Quelle