Reaction #7785

Reaction equation

3-cyano-phenylboronic acid

2-(3-bromo-4-methylphenyl)-1,3-benzoxazole

triphenylphosphine

potassium carbonate

→

5′-(1,3-benzoxazol-2-yl)-2′-methyl-1,1′-biphenyl-3-carbonitrile

Solvents

DME H2O

Conditions

Workup

1. 1
   TemperatureThe mixture was cooled to rt
2. 2
   Otherthe two layers were separated
3. 3
   Extractionthe aqueous layer was extracted with EtOAc (3×)
4. 4
   Dryingdried over Na2SO4
5. 5
   Otherevaporated to dryness
6. 6
   Otherto give a clear solid
7. 7
   OtherPurification of the crude by flash chromatography on silica gel eluting with a gradient of EtOAc

Procedure

A mixture of 3-cyano-phenylboronic acid (183 mg, 1.3 mmol), 2-(3-bromo-4-methylphenyl)-1,3-benzoxazole (300 mg, 1.04 mmol), dichlorobis(triphenylphosphine)palladium(II) (36.5 mg, 0.052 mmol), triphenylphosphine (27 mg, 0.104 mmol), and potassium carbonate (287 mg, 2.08 mmol) in degassed DME/H2O (5:1, 18 mL) was heated to 80° C. for 18 h. The mixture was cooled to rt and the two layers were separated and the aqueous layer was extracted with EtOAc (3×). The organics were combined, dried over Na2SO4, and evaporated to dryness to give a clear solid. Purification of the crude by flash chromatography on silica gel eluting with a gradient of EtOAc:hexanes (0 to 30 min: 0 to 20% EtOAc) afforded 5′-(1,3-benzoxazol-2-yl)-2′-methyl-1,1′-biphenyl-3-carbonitrile a colorless solid.

Source