Reaktion #559031

Reaktionsgleichung

1,1-dimethylethyl {2-[(4-bromo-3-methylphenyl)oxy]ethyl}carbamate

1,1-Dimethylethyl {2-[(4-bromo-3-methylphenyl)oxy]ethyl}carbamate

3-(aminocarbonyl)phenylboronic acid

CH2Cl2

Na2CO3

→

title compound

1,1-Dimethylethyl (2-{[3′-(aminocarbonyl)-2-methyl-4-biphenylyl]oxy}ethyl)carbamate

Lösungsmittel

DME

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeby sparging with N2, (5-10 min)
2. 2
   TemperaturUpon cooling
3. 3
   workup.ADDITIONthe mixture was diluted with EtOAc
4. 4
   Waschenwashed (water, brine)
5. 5
   Trocknendried over Na2SO4
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe residue was purified by flash chromatography (EtOAc/hexanes)

Vorschrift

A mixture of 1,1-dimethylethyl {2-[(4-bromo-3-methylphenyl)oxy]ethyl}carbamate (0.102 g, 0.31 mmol; Example V-15), 3-(aminocarbonyl)phenylboronic acid (0.056 g; 0.34 mmol), PdCl2(dppf).CH2Cl2 (0.0075 g; 0.01 mmol), DME (2 mL) and 2M Na2CO3 (2 mL) was degassed by sparging with N2, (5-10 min) then stirred at 80° C. for 5.5 h. Upon cooling, the mixture was diluted with EtOAc washed (water, brine), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a colorless foam. LC/MS (method A) 2.59 min, m/z 371 (M+1, 2%), 392 (M+Na, 53%), 271 ([M−Boc]+H, 100%).

Quelle