Reaktion #155769

Reaktionsgleichung

t-butyl 2-(2-bromo-4-((4-fluoro-N-methylphenylsulfonamido)methyl)phenoxy)acetate

3-cyanobenzeneboronic acid

potassium carbonate

→

t-butyl 2-(2-(3-cyanophenyl)-4-((4-fluoro-N-methylphenylsulfonamido)methyl)phenoxy)acetate

Ausbeute 59.8%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenAfter concentration in vacuo
2. 2
   Extraktionthe residue was extracted between EtOAc (100 ml) and brine (100 mL)
3. 3
   TrocknenThe separated EtOAc layer was dried (Na2SO4)
4. 4
   Einengenconcentrated
5. 5
   Sonstigepurified via silica gel chromatography (linear gradient of 0% EtOAc/hexanes to 100% EtOAc/hexanes)

Vorschrift

To a DMF (50 mL) solution of t-butyl 2-(2-bromo-4-((4-fluoro-N-methylphenylsulfonamido)methyl)phenoxy)acetate (3) (1.25 g, 2.6 mmol, 1 eq) was added 3-cyanobenzeneboronic acid (0.57 g, 3.8 mmol, 1.5 eq, Frontier Scientific, Inc., Logan, Utah, USA), potassium carbonate (1 g, 7.7 mmol, 3 eq), and tetrakis(triphenylphoshine)palladium (0.15 g, 0.13 mmol, 0.05 eq). The mixture was stirred at 90° C. for 18 h. After concentration in vacuo, the residue was extracted between EtOAc (100 ml) and brine (100 mL). The separated EtOAc layer was dried (Na2SO4), concentrated and purified via silica gel chromatography (linear gradient of 0% EtOAc/hexanes to 100% EtOAc/hexanes) to yield 0.78 g (59.8%) of t-butyl 2-(2-(3-cyanophenyl)-4-((4-fluoro-N-methylphenylsulfonamido)methyl)phenoxy)acetate (4). 1HNMR (CDCl3, 300 MHz): δ 7.80 (m, 4H), 7.58 (m, 1H), 7.48 (t, 1H), 7.21 (m, 4H), 6.79 (d, 1H), 4.52 (s, 2H), 4.11 (s, 2H), 2.61 (s, 3H), 1.45 (s, 9H).

Quelle