Реакция #84067

Уравнение реакции

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

TMSN3

→

Compound 11

Выход 13.5%

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

Выход 13.5%

Растворители

toluene

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was heated
2. 2
   Температураto reflux overnight
3. 3
   ДругоеThe volatiles were removed under reduced pressure
4. 4
   ДругоеThe residue was purified by prep-HPLC

Методика

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]+.

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