Potassium Carbonate → (E)-tert-butyl 2-chloro-5-(2-cyclopropylvinyl)phenylcarbamate

HRID 1259190

Reaktionsgleichung

Reaktionsgleichung von HRID 1259190
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:16])=[C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:7]=1.[CH:17]1(/[CH:20]=[CH:21]/B2OC(C)(C)C(C)(C)O2)[CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.CCOC(C)=O.O>[Cl:16][C:5]1[CH:4]=[CH:3][C:2](/[CH:21]=[CH:20]/[CH:17]2[CH2:19][CH2:18]2)=[CH:7][C:6]=1[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 16217940(E)-2-Cyclopropylethylene-1-boronic acid, pinacol esterHCID 57840526tert-butyl N-(5-bromo-2-chlorophenyl)carbamate

Produkt 1

HCID 66875036(E)-tert-butyl 2-chloro-5-(2-cyclopropylvinyl)phenylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of tert-butyl 5-bromo-2-chlorophenylcarbamate (from the previous step) (1.0 eq.) and (E)-2-(2-cyclopropylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (commercially available) (1.0 eq.) in toluene (0.2 M) was mixed with tetrakis(triphenyl-phosphine)palladium (5 mol %) and 2N aqueous potassium carbonate solution (2.0 eq.). The reaction was heated to 100° C. and stirred overnight. After cooling to ambient temperature, the reaction mixture was diluted with EtOAc and water. The two phases were separated, and the aqueous layer was extracted twice with EtOAc. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vaccuo. The crude product was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-5% EtOAc/Hexanes to give (E)-tert-butyl 2-chloro-5-(2-cyclopropylvinyl)phenylcarbamate as a pale yellow solid.

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. customThe two phases were separated
  3. extractionthe aqueous layer was extracted twice with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated en vaccuo
  7. customThe crude product was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Quellen und Nachweise

ORD-Eintrag
ord-40c21e82630c46babb4cae01df42910b
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466167B2

Verknüpfte Notizen

Wird geladen…