Reaction #5774

Reaction equation

potassium carbonate

5-(2-bromophenyl)-1-(4-nitrophenyl)-1H-tetrazole

water

2-(4-[(2-Ethylquinolin-4-yloxy)-methyl]phenyl)-5,5-dimethyl-1,3,2-dioxaborinane

→

2-ethyl-4-[(2'-(1-(4-nitrophenyl)-1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]quinoline

Yield 58.2%

Solvents

methanol

toluene

toluene

Conditions

Workup

1. 1
   Otherto give a clear solution
2. 2
   Temperaturethe reaction mixture heated
3. 3
   Temperatureat reflux for 6 hours
4. 4
   Temperatureto cool
5. 5
   OtherThe organic phase was separated
6. 6
   Extractionthe aqueous phase extracted with toluene (2×20 ml)
7. 7
   OtherThe combined organic phases were evaporated
8. 8
   Otherthe resultant solid recrystallised from toluene

Procedure

A mixture of potassium carbonate (1.08 g; 7.8 mmol), 5-(2-bromophenyl)-1-(4-nitrophenyl)-1H-tetrazole (1.16 g; 3.2 mmol) water (10 ml), toluene (10 ml), and methanol (10 ml) was heated to 60° C. to give a clear solution. 2-(4-[(2-Ethylquinolin-4-yloxy)-methyl]phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (1.0 g; 2.6 mmol) and tetrakis(triphenylphosphine)palladium (0.06 g; 0.05 mmol) were added and the reaction mixture heated at reflux for 6 hours. The mixture was allowed to cool and further toluene (10 ml) added. The organic phase was separated and the aqueous phase extracted with toluene (2×20 ml). The combined organic phases were evaporated and the resultant solid recrystallised from toluene to give 2-ethyl-4-[(2'-(1-(4-nitrophenyl)-1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]quinoline as a solid (0.8 g); m.p. and NMR similar to that of the product of Example 5.

Source