Réaction #84067

Équation de réaction

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

TMSN3

→

Compound 11

Rendement 13.5%

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

Rendement 13.5%

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was heated
2. 2
   Températureto reflux overnight
3. 3
   AutreThe volatiles were removed under reduced pressure
4. 4
   AutreThe residue was purified by prep-HPLC

Mode opératoire

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