Potassium Carbonate → (E)-ethyl 3-(3-(tert-butoxycarbonylamino)-4-chlorophenyl)acrylate

HRID 631169

Reaktionsgleichung

Reaktionsgleichung von HRID 631169
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.C([O-])([O-])=O.[K+].[K+].CC1(C)C(C)(C)OB(/[CH:31]=[CH:32]/[C:33]([O:35][CH2:36][CH3:37])=[O:34])O1>C(#N)C.CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:11]([O:10][C:9]([NH:8][C:6]1[CH:7]=[C:2](/[CH:31]=[CH:32]/[C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:3]=[CH:4][C:5]=1[Cl:16])=[O:15])([CH3:14])([CH3:13])[CH3:12]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 23553751(E)-Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylateHCID 57840526tert-butyl N-(5-bromo-2-chlorophenyl)carbamate

Produkt 1

HCID 67067541(E)-ethyl 3-(3-(tert-butoxycarbonylamino)-4-chlorophenyl)acrylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of tert-butyl 5-bromo-2-chlorophenylcarbamate (1) (1.0 equiv.) in acetonitrile (0.3M) and EtOH (0.5M) was added K2CO3 (2.0 equiv.). The reaction was degassed and flushed with N2, then added (E)-ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate (2) (1.2 equiv.) and Pd(PPh3)4 (0.1 equiv.). The reaction was flushed again with N2 and stirred at 100° C. overnight. After cooling to room temperature, hexane was added, and the mixture was filtered through a pad of silica, eluting with EA/Hex (1:1) until the product was completely eluted. The filtrate was concentrated and purified on Combiflash, eluting with 0-15% EA in Hex to give (E)-ethyl 3-(3-(tert-butoxycarbonylamino)-4-chlorophenyl)acrylate (3) as a white solid.

Aufarbeitung

  1. customThe reaction was degassed
  2. customflushed with N2
  3. customThe reaction was flushed again with N2
  4. temperatureAfter cooling to room temperature
  5. additionhexane was added
  6. filtrationthe mixture was filtered through a pad of silica
  7. washeluting with EA/Hex (1:1) until the product
  8. washwas completely eluted
  9. concentrationThe filtrate was concentrated
  10. custompurified on Combiflash
  11. washeluting with 0-15% EA in Hex

Quellen und Nachweise

ORD-Eintrag
ord-0ce24bd14d2d4f8bbfdf1f8e2b30fd60
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09320748B2

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