Potassium Carbonate → Tert-butyl(trans)-2-(3'-chlorobiphenyl-4-yl)cyclopropylcarbamate

HRID 1023820Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1023820
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:10][C@H:9]2[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.O>[Cl:19][C:20]1[CH:25]=[C:24]([C:2]2[CH:7]=[CH:6][C:5]([C@@H:8]3[CH2:10][C@H:9]3[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][CH:3]=2)[CH:23]=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 86658779tert-butyl ((1R,2S)-2-(4-bromophenyl)cyclopropyl)carbamate2×

Produkt 1

HCID 86680872Tert-butyl(trans)-2-(3'-chlorobiphenyl-4-yl)cyclopropylcarbamateAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Versuchsvorschrift

A solution of tert-butyl (trans)-2-(4-bromophenyl)cyclopropylcarbamate (Intermediate H, 3 g, 9.6 mmol), 3-chlorophenylboronic acid (1.8 g, 11.5 mmol) and K2CO3 (3.9 g, 28.8 mmol) in acetonitrile:water (4:1) was degassed for 20 min. Tetrakis triphenylphosphine palladium (300 mg) was added and heated at reflux for 18 h. After completion, the reaction mixture was poured into ice water (100 mL) and extracted with EtOAc (2×50 mL). The combined organic extracts were washed with water (50 mL), brine (50 mL) and dried over anhydrous Na2SO4 filtered and evaporated. The crude residue was purified by column chromatography (SiO2) using EtOAc: Pet ether to give (3 g, 91%) tert-butyl (trans)-2-(3′-chlorobiphenyl-4-yl)cyclopropylcarbamate as a white solid.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 18 h
  3. extractionextracted with EtOAc (2×50 mL)
  4. washThe combined organic extracts were washed with water (50 mL), brine (50 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude residue was purified by column chromatography (SiO2)

Quellen und Nachweise

ORD-Eintrag
ord-fe25649eba4b429a8a8fca3560739bf3
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722743B2

Notizen zur Reaktion

Wird geladen…