Reaction #84067

Reaction equation

4-(4-chloro-6-hydroxyquinolin-2-yl)benzonitrile

TMSN3

→

Compound 11

Yield 13.5%

2-(4-(2H-tetrazol-5-yl)phenyl)-4-chloroquinolin-6-ol

Yield 13.5%

Solvents

toluene

Conditions

Workup

1. 1
   TemperatureThe mixture was heated
2. 2
   Temperatureto reflux overnight
3. 3
   OtherThe volatiles were removed under reduced pressure
4. 4
   OtherThe residue was purified by prep-HPLC

Procedure

Followed Scheme 4, route A. To a solution of 4-(4-chloro-6-hydroxyquinolin-2-yl)benzonitrile (65 mg, 0.23 mmol) in toluene (2 mL), was added TMSN3 (455 mg, 4.18 mmol) and Bu2SnO (15 mg, 0.069 mmol) at room temperature. The mixture was heated to reflux overnight. The volatiles were removed under reduced pressure. The residue was purified by prep-HPLC to afford Compound 11 (10 mg, 13.5%). 1H NMR (MeOD-d4, 500 MHz): δ 8.34 (d, J=8.5 Hz, 2H), 8.21 (s, 1H), 8.19 (s, 2H), 8.07 (d, J=9.0 Hz, 1H), 7.51 (d, J=2.5 Hz, 1H), 7.47 (dd, J=2.5 Hz, J=9.5 Hz, 1H). MS (ESI): m/z 324.0 [M+1]+.

Source