Potassium Carbonate → (4'-Cyano-biphenyl-3-yl)-carbamic acid tert-butyl ester

HRID 39152Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 39152
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)#[N:2].[C:12]([O:16][C:17](=[O:26])[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21](Br)[CH:20]=1)([CH3:15])([CH3:14])[CH3:13].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.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:12]([O:16][C:17](=[O:26])[NH:18][C:19]1[CH:24]=[C:23]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH:22]=[CH:21][CH:20]=1)([CH3:15])([CH3:13])[CH3:14]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 2757254N-(tert-Butoxycarbonyl)-3-bromoaniline

Produkt 1

HCID 67120680(4'-Cyano-biphenyl-3-yl)-carbamic acid tert-butyl esterAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 21962138N,N-Dimethylformamide--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 4-cyanobenzeneboronic acid (14.7 g, 0.10 mol), 3-bromo-phenyl-carbamic acid tert-butyl ester (27.2 g, 0.10 mol), Pd(Ph3P)4 (11.6 g, 0.01 mol) and K2CO3 (21 g, 0.15 mol) in DMF/H2O (1:1, 350 mL) was stirred under argon at 80° C. overnight. The DMF was evaporated under reduced pressure, and the residue was dissolved in EtOAc (200 mL). The mixture was washed with water and brine, dried over Na2SO4, and concentrated to dryness. The residue was purified by column chromatography (petroleum ether/EtOAc 50:1) on silica gel to give (4′-cyano-biphenyl-3-yl)-carbamic acid tert-butyl ester (17 g, 59%). 1H NMR (300 MHz, DMSO-d6) δ 9.48 (s, 1H), 7.91 (d, J=8.4 Hz, 2H), 7.85 (s, 1H), 7.76 (d, J=8.4 Hz, 2H), 7.32-7.48 (m, 3H), 1.47 (s, 9H).

Aufarbeitung

  1. customThe DMF was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc (200 mL)
  3. washThe mixture was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by column chromatography (petroleum ether/EtOAc 50:1) on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-9af1eaa78cff4df991ec063efe62c212
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524767B2

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