Reaction #5771

Reaction equation

potassium carbonate

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

Compound B

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

toluene

methanol

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 combined organic phases were evaporated
8. 8
   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) (Compound B), 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 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 (4.3 g); NMR (CDCl3): 1.42(3H,t), 3.0(2H,q), 5.23(2H,s), 6.67(2H,d), 6.75(1H,s), 6.85(2H,d), 7.25 (2H,d), 7.43(1H,d), 7.55(1H,t), 7.70(3H,m), 7.90(3H,d), 8.05(1H,d), 8.20(1H,d).

Source