Reaktion #157490

Reaktionsgleichung

m-cyanophenyl boronic acid

1,1-dimethylethyl {2-[(4-bromophenyl)oxy]ethyl}(4,4-dimethylcyclohexyl)carbamate

→

title compound

1,1-dimethylethyl {2-[(3′-cyano-4-biphenylyl)oxy]ethyl}(4,4-dimethylcyclohexyl)carbamate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeCH2Cl2, 2M Na2CO3 (4 mL) and DME (4 mL) was sparged 5 min with N2
2. 2
   TemperaturUpon cooling
3. 3
   workup.ADDITIONthe mixture was diluted with EtOAc
4. 4
   Waschenwashed with water
5. 5
   Extraktionthe washing was back-extracted with EtOAc (×2)
6. 6
   WaschenCombined organics were washed (water, brine)
7. 7
   Trocknendried over Na2SO4
8. 8
   Sonstigepurified by flash chromatography (EtOAc/hexanes)

Vorschrift

A mixture of m-cyanophenyl boronic acid (0.086 g; 0.59 mmol), 1,1-dimethylethyl {2-[(4-bromophenyl)oxy]ethyl}(4,4-dimethylcyclohexyl)carbamate (0.250 g; 0.59 mmol; Example V-8), PdCl2(dppf).CH2Cl2, 2M Na2CO3 (4 mL) and DME (4 mL) was sparged 5 min with N2 and then heated to 80° C. for 5 h. Upon cooling, the mixture was diluted with EtOAc, washed with water and the washing was back-extracted with EtOAc (×2). Combined organics were washed (water, brine), dried over Na2SO4, adsorbed onto a minimal amount of silica gel and purified by flash chromatography (EtOAc/hexanes), affording the title compound as a colorless gum. 1H NMR (400 MHz, CDCl3) δ 0.92 (s, 3H), 0.94 (s, 3H, partially overlapping 0.92), 1.21-1.87 (m, 17H), 3.45-3.63 (m, 2H), 3.88 (br. s, 1H), 4.10 (br. s, 2H), 7.00 (m, 2H), 7.49 (m, 2H), 7.52 (d, J=7.8 Hz, 1H; partially overlapping 7.49), 7.58 (d, J=7.6 Hz, 1H), 7.77 (partially resolved ddd, Jortho=7.8 Hz, 1H), 7.82 (unresolved dd, 1H).

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