Reaction #574598

Reaction equation

potassium carbonate

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

water

4-[(2-Ethylquinolin-4-yloxy)methyl]phenylboronic acid hydrochloride

→

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

Yield 65.0%

Solvents

methanol

toluene

toluene

Conditions

Workup

1. 1
   Otherto give a clear solution
2. 2
   Temperaturethe reaction mixture heated
3. 3
   Temperatureat reflux for 4 hours
4. 4
   Temperatureto cool
5. 5
   OtherThe organic phase was separated
6. 6
   Extractionthe aqueous phase extracted with toluene (2×50 ml)
7. 7
   Otherthe resultant solid recrystallised from toluene

Procedure

A mixture of potassium carbonate (5.8 g), 5-(2-bromophenyl)-1-(4-nitrophenyl)-1H-tetrazole (5.81 g) (obtained as described in Procedure A, step (ii)), water (43 ml), toluene (43 ml), and methanol (43 ml) was heated to 60° C. to give a clear solution. 4-[(2-Ethylquinolin-4-yloxy)methyl]phenylboronic acid hydrochloride (4.3 g) and tetrakis(triphenylphosphine)palladium (0.032 g) were added and the reaction mixture heated at reflux for 4 hours. The mixture was allowed to cool and further toluene (50 ml) added. The organic phase was separated and the aqueous phase extracted with toluene (2×50 ml). The combined organic phases were evaported 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 (A) as a solid (4.3 g); m.p. and NMR similar to that of compound A of Procedure A, part (v).

Source