Reaction #5776

Reaction equation

Triethylamine

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

2-bromobenzonitrile

→

4'-[(2-ethylquinolin-4-yloxy)methyl]biphenyl-2-carbonitrile

Yield 91.1%

Solvents

butanol

water

Conditions

Workup

1. 1
   Temperaturethe mixture was heated
2. 2
   Temperatureat reflux for 3 hours
3. 3
   FiltrationThe hot reaction mixture was filtered through diatomaceous earth
4. 4
   TemperatureThe mixture was then cooled to 4° C. for 30 minutes
5. 5
   OtherThe solid which crystallised
6. 6
   Filtrationwas collected by filtration
7. 7
   Washwashed with cold butanol (16 ml) and water (2×16 ml)
8. 8
   Otherdried at 55° C.

Procedure

Triethylamine (13.8 ml) was added to a mixture of 4-[(2-ethylquinolin-4-yloxy)methyl]phenylboronic acid hydrochloride (12.74 g), 2-bromobenzonitrile (5.92 g) and palladium chloride (0.13 g) in butanol (80 ml) and water (40 ml) and the mixture was heated at reflux for 3 hours. The hot reaction mixture was filtered through diatomaceous earth and the filtrate was stirred while allowing to cool to ambient temperature. The mixture was then cooled to 4° C. for 30 minutes. The solid which crystallised was collected by filtration, washed with cold butanol (16 ml) and water (2×16 ml) and then dried at 55° C. to give 4'-[(2-ethylquinolin-4-yloxy)methyl]biphenyl-2-carbonitrile (10.8 g); m.p. 161°-162° C.; NMR (CDCl3): 1.4(t,3H), 2.97(q,2H), 5.35(s,2H), 6.76(s,1H), 7.4-7.6(m,3H), 7.6-7.8(m,6H), 8.0(d,1 H), 8.25(d,1H).

Source